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Abstract:

The invention relates to 2-(benzylsulfonyl)-oxazole derivatives, chiral
2-(benzylsulfinyl)-oxazole derivatives and 2-(benzylsulfanyl)-oxazole
derivatives of general formula (I) and the salts thereof, wherein the
individual radicals and indexes have the meaning indicated in the
description. Also described are methods for the production thereof as
well as the use of said compounds as herbicides and plant growth
regulators, in particular as herbicides for selectively controlling weeds
in plant crops.

Claims:

1. A compound of the formula (I) or an agrochemically acceptable salt
thereof ##STR00044## in which n is 0, 1, 2; the substituents R1
and R2 are each independently of one another selected from the group
consisting of hydrogen, halogen, nitro, cyano, formyl, --C(O)OH,
hydroxyl, and amino; (C1-C6)-alkyl,
(C1-C6)-alkylcarbonyl,
(C1-C6)-alkylcarbonyl-(C1-C4)-alkyl and
(C1-C6)-alkylcarbonyloxy; (C1-C6)-alkoxy,
(C1-C6)-alkoxy-carbonyl,
(C1-C6)-alkoxycarbonyl-(C1-C6)-alkyl,
(C1-C6) alkoxy-(C1-C6)-alkyl,
(C1-C6)-alkoxy-(C1-C6)-alkoxy and
(C1-C6)-alkoxy-car-bonyl-(C1-C6)-alkoxy;
(C2-C6)-alkenyl, (C2-C6)-alkenyloxy,
(C2-C6)-alkynyl and (C2-C6)-alkynyloxy;
(C1-C6)-alkylthio, (C1-C6)-alkylsulfinyl,
(C1-C6)-alkylsulfonyl, (C1-C6)-alkylsulfonyloxy,
(C1-C6)-alkylsulfonyl-(C1-C6)-alkyl,
(C1-C6)-alkyl sulfinyl-(C1-C6)-alkyl,
(C1-C6)-alkylthio-(C1-C6)-alkyl and
(C1-C6)-alkylthio-(C1-C6)-alkoxy;
mono-((C1-C6)-alkyl)amino, di-((C1-C6)-alkyl)amino,
N--((C1-C6)-alkanoyl)amino,
aminocarbonyl-(C1-C6)-alkyl,
mono-((C1-C6)-alkyeaminocarbonyl,
di-((C1-C6)-alkyeaminocarbonyl,
mono-((C1-C6)-alkyl)aminosulfonyl and
di-((C1-C6)-alkyl)aminosulfonyl; (C3-C8)-cycloalkyl,
(C3-C8)-cycloalkoxy,
(C3-C8)-cycloalkyl-(C1-C6)-alkyl,
(C3-C8)-cycloalkyl-(C1-C6)-alkoxy,
(C3-C8)-cycloalkylcarbonyl and
(C3-C8)-cycloalkoxycarbonyl; (C3-C8)-cycloalkenyl,
(C3-C8)-cycloalkenyloxy, (C3-C8)-cycloalkylthio,
(C3-C8)-cycloalkylsulfinyl,
(C3-C8)-cycloalkylsulfonyl and
(C3-C8)-cycloalkylsulfonyloxy; cyano-(C1-C6)-alkoxy
and cyano-(C1-C6)-alkyl;
--CONH--SO2--(C1-C6)-alkyl, --NHCHO,
--NHCO--(C1-C6)-alkyl, --NHCO2--(C1-C6)-alkyl,
--NHCONH--(C1-C6)-alkyl, --NHSO2--(C1-C6)-alkyl,
--OCONH--(C1-C6)-alkyl,
(C1-C6)-alkylaminosulfonyl-(C1-C2)-alkyl,
di-(C1-C6)-alkylaminosulfonyl-(C1-C2)-alkyl,
--C(O)NHR9, --C(O)NR9R10, where R9 and R10 are
each independently of one another selected from the group consisting of
hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl,
(C1-C6)-haloalkyl, or where R9 and R10 together form
a (C1-C6)-alkylene group which may contain an oxygen or a
sulfur atom or one or two amino or (C1-C6)-alkylamino groups,
the substituents R3 to R7 are each independently of one another
selected from the group consisting of hydrogen, halogen, hydroxyl, cyano,
nitro, amino, C(O)OH and formyl; (C1-C6)-alkyl,
(C1-C6)-haloalkyl, (C1-C6)-alkylcarbonyl,
(C1-C6)-haloalkylcarbonyl, (C1-C6)-alkylcarbonyloxy,
(C1-C6)-haloalkylcarbonyloxy,
(C1-C6)-alkylcarbonyl-(C1-C4)-alkyl,
(C1-C6)-haloalkylcarbonyl-(C1-C4)-alkyl,
(C1-C6)-alkylcarbonyl-(C1-C4)-haloalkyl and
(C1-C6)-haloalkylcarbonyl-(C1-C4)-haloalkyl;
(C1-C6)-alkoxy, (C1-C6)-haloalkoxy,
(C1-C6)-alkoxycarbonyl, (C1-C6)-haloalkoxycarbonyl,
(C1-C6)-alkoxycarbonyl-(C1-C6)-alkyl,
(C1-C6)-haloalkoxycarbonyl-(C1-C6)-alkyl,
(C1-C6)-alkoxycarbonyl-(C1-C6)-haloalkyl and
(C1-C6)-haloalkoxycarbonyl-(C1-C6)-haloalkyl;
(C2-C6)-alkenyl, (C2-C6)-haloalkenyl,
(C2-C6)-alkenylcarbonyl, (C2-C6)-haloalkenylcarbonyl,
(C2-C6)-alkenyloxy, (C2-C6)-haloalkenyloxy,
(C2-C6)-alkenyloxycarbonyl and
(C2-C6)-haloalkenyloxycarbonyl; (C2-C6)-alkynyl,
(C2-C6)-haloalkynyl, (C2-C6)-alkynylcarbonyl,
(C2-C6)-haloalkynylcarbonyl, (C2-C6)-alkynyloxy,
(C2-C6)-haloalkynyloxy, (C2-C6)-alkynyloxycarbonyl
and (C2-C6)-haloalkynyloxycarbonyl;
(C1-C6)-alkylthiocarbonyl,
(C1-C6)-haloalkylihiocarbonyk
(C1-C6)-alkylthiocarbonyloxy and
(C1-C6)-halo-al-kyl-thio-carbonyloxy;
(C1-C6)-alkylthio-(C1-C6)-alkoxy,
(C1-C6)-alkylthio-(C1-C6)-alkylcarbonyl and
(C1-C6)-alkylthio-(C1-C6)-alkylcarbonyloxy;
(C1-C6)-alkylsulfonyl, (C1-C6)-alkylthio,
(C1-C6)-alkylsulfinyl, (C1-C6)-haloalkylsulfonyl,
(C1-C6)-haloalkylthio, (C1-C6)-halo-alkylsulfinyl,
(C1-C6)-alkylsulfonyl-(C1-C6)-alkyl,
(C1-C6)-alkyl-thio-(C1-C6)-alkyl,
(C1-C6)-alkylsulfinyl-(C1-C6)-alkyl,
(C1-C6)-haloalkylsulfonyl-(C1-C6)-alkyl,
(C1-C6)-haloalkylthio-(C1-C6)-alkyl,
(C1-C6)-haloalkylsulfinyl-(C1-C6)-alkyl,
(C1-C6)-alkylsulfonyl-(C1-C6)-haloalkyl,
(C1-C6)-alkylthio-(C1-C6)-haloalkyl,
(C1-C6)-alkylsulfinyl-(C1-C6)-haloalkyl,
(C1-C6)-haloalkylsulfonyl-(C1-C6)-haloalkyl,
(C1-C6)-haloalkylthio-(C1-C6)-haloalkyl,
(C1-C6)-haloalkylsultinyl-(C1-C6)-haloalkyl,
(C1-C6)-alkylsulfonyloxy and
(C1-C6)-haloalkylsulfonyloxy;
mono-((C1-C6)-alkyl)amino,
mono-((C1-C6)-haloalkyl)amino,
di-((C1-C6)-alkyl)amino, di-((C1-C6)-haloalkyl)amino,
((C1-C6)-alkyl-(C1-C6)-haloalkyl)amino,
N--((C1-C6)-alkanoyl)amino,
N--((C1-C6)-haloalkanoyl)amino,
aminocarbonyl-(C1-C6)-alkyl,
mono-(C1-C6)-alkylaminocarbonyl-(C1-C6)-alkyl,
di-(C1-C6)-alkylaminocarbonyl-(C1-C6)-alkyl and
mono-((C1-C6)-alkyl)aminocarbonyl; (C1-C6)-alkoxy
--(C1-C6)-alkyl,
(C1-C6)-alkoxy-(C1-C6)-alkoxy,
(C1-C6)-alkoxycarbonyl-(C1-C6)-alkoxy,
(C3-C8)-cycloalkyl, (C3-C8)-cycloalkoxy,
(C3-C8)-cycloalkyl-(C1-C6)-alkyl,
(C3-C8)-cycloalkyl-(C1-C6)-haloalkyl,
(C3-C8)-cycloalkyl-(C1-C6)-alkoxy,
(C3-C8)-cycloalkyl-(C1-C6)-haloalkoxy,
(C3-C8)-cycloalkylcarbonyl,
(C3-C8)-cycloalkoxycarbonyl,
(C3-C8)-cycloalkyl-(C1-C6)-alkylcarbonyl,
(C3-C8)-cycloalkyl-(C1-C6)-haloalkylcarbonyl,
(C3-C8)-cycloalkyl-(C1-C6)-alkoxycarbonyl,
(C3-C8)-cycloalkyl-(C1-C6)-haloalkoxycarbonyl,
(C3-C8)-cyclo-alkylcarbonyloxy,
(C3-C8)-cycloalkoxycarbonyloxy,
(C3-C8)-cycloalkyl-(C1-C6)-alkyl-carbonyloxy,
(C3-C8)-cycloalkyl-(C1-C6)-haloalkylcarbonyloxy,
(C3-C8)-cycloalkyl-(C1-C6)-alkoxycarbonyloxy and
(C3-C8)-cycloalkyl-(C1-C6)-halo-alkoxycarbonyloxy;
(C3-C8)-cycloalkenyl, (C3-C8)-cycloalkenyloxy,
(C3-C8)-cycloalkenyl-(C1-C6)-alkyl,
(C3-C8)-cycloalkenyl-(C1-C6)-haloalkyl,
(C3-C8)-cycloalkenyl-(C1-C6)-alkoxy,
(C3-C8)-cycloalkenyl-(C1-C6)-haloalkoxy,
(C3-C8)-cycloalkenylcarbonyl,
(C3-C8)-cycloalkenyloxycarbonyl,
(C3-C8)-cycloalkenyl-(C1-C6)-alkylcarbonyl,
(C3-C8)-cycloalkenyl-(C1-C6)-haloalkylcarbonyl,
(C3-C8)-cycloalkenyl-(C1-C6)-alkoxycarbonyl,
(C3-C8)-cycloalkenyl-(C1-C6)-haloalkoxycarbonyl,
(C3-C8)-cycloalkenylcarbonyloxy,
(C3-C8)-cycloalkenyloxycarbonyloxy,
(C3-C8)-cycloalkenyl-(C1-C6)-alkylcarbonyloxy,
(C3-C8)-cycloalkenyl-(C1-C6)-haloalkyl-carbonyloxy,
(C3-C8)-cycloalkenyl-(C1-C6)-alkoxycarbonyloxy and
(C3-C8)-cycloalkenyl-(C1-C6)-haloalkoxycarbonyloxy;
(C3-C8)-cycloalkylthio-(C3-C8)-alkenylthio,
(C3-C8)-cyclo-alkenylthio and (C3-C6)-alkynylthio;
hydroxy-(C1-C6)-alkyl, hydroxy-(C1-C6)-alkoxy,
cyano-(C1-C6)-alkoxy and cyano-(C1-C6)-alkyl;
3-oxetanyloxy-, --C(O)NHR9 or --C(O)NR9R10, where R9
and R10 are each independently of one another selected from the
group consisting of hydrogen, (C1-C6)-alkyl,
(C3-C6)-cycloalkyl, (C1-C6)-haloalkyl, or where
R9 and R10 together form a (C1-C6)-alkylene group
which may contain an oxygen or a sulfur atom or one or two amino or
(C1-C6)-alkylamino groups, wherein (1) the radicals defined
above for R3 to R7 may optionally be cyclically attached to one
another, with the proviso that they are ortho to one another; and/or (2)
two substituents which are ortho to one another together form a
(C1-C6)-alkylene group which may contain one or more oxygen
and/or sulfur atoms, where the (C1-C6)-alkylene group may be
mono- or polysubstituted by halogen and the respective halogen
substituents may be identical or different; and/or (3) the radicals
R1 and R2 mentioned above may be mono- or polysubstituted and
independently of one another may be substituted by radicals selected from
the group consisting of halogen and (C1-C6)-alkyl; and (4) at
least one radical selected from the group of the radicals R to R is not
hydrogen, except for the compound
2-[(1,3-benzodioxol-5-ylmethyl)sulfanyl]-4-methyl-1,3-oxazole.

2. A compound of the formula (I), its agrochemically acceptable salt or
its agrochemically acceptable quaternized nitrogen derivative as claimed
in claim 1, wherein the radical R is selected from the group consisting
of hydrogen, halogen, nitro, cyano, carboxyl, (C1-C6)-alkyl,
(C3-C6)-cycloalkyl, (C3-C6)-cycloalkoxy,
(C1-C6-alkoxy, (C1-C6)-alkylcarbonyl,
(C3-C6)-cycloalkylcarbonyl, (C1-C6)-alkoxycarbonyl,
(C3-C6)-cycloalkoxycarbonyl,
mono-((C1-C4)-alkyl)aminocarbonyl,
di-((C1-C4)-alkyl)amino carbonyl,
mono-((C1-C4)-alkyl)amino sulfonyl,
di-((C1-C4)-alkyl)aminosulfonyl, (C1-C4)-alkyl-thio,
(C3-C6)-cycloalkylthio, (C1-C4)-alkylsulfinyl,
(C3-C6)-cycloalkylsulfinyl, (C1-C4)-alkylsulfonyl,
(C3-C6)-cycloalkylsulfonyl, (C1-C4)-alkylsulfonyloxy,
(C3-C6)-cycloalkylsulfonyloxy, (C2-C3)-alkenyl,
(C2-C3)-alkynyl, (C2-C3)-alkenyloxy,
(C2-C3)-alkynyloxy, --NHCO--(C1-C3)-alkyl,
--NHCO2--(C1-C3)-alkyl, --NHCONH--(C1-C3)-alkyl,
--NHSO2--(C1-C3)-alkyl, --OCONH--(C1-C3)-alkyl,
--CONHR9, --CONR9R10, where R9 and R10
independently of one another selected from the group consisting of
hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl and
(C1-C6)-haloalkyl; and where the radical R1 may be mono-
or polysubstituted by radicals selected from the group consisting of
halogen and (C1-C6)-alkyl.

3. A compound of the formula (I), its agrochemically acceptable salt or
its agrochemically acceptable quaternized nitrogen derivative as claimed
in claim 1, wherein the radical R2 is selected from the group
consisting of hydrogen, halogen, nitro, cyano, carboxyl,
(C1-C6)-alkyl, (C3-C6)-cycloalkyl,
(C3-C6)-cycloalkoxy, (C1-C6)-alkoxy,
(C1-C6)-alkylcarbonyl, (C3-C6)-cycloalkylcarbonyl,
(C1-C6)-alkoxycarbonyl, (C3-C6)-cycloalkoxycarbonyl,
mono-((C1-C4)-alkyl)aminocarbonyl,
di-((C1-C4)-alkyl)aminocarbonyl,
mono-((C1-C4)-alkyl)aminosulfonyl,
di-((C1-C4)-alkyl)aminosulfonyl, (C1-C4)-alkyl-thio,
(C3-C6)-cycloalkylthio, (C1-C4)-alkylsulfinyl,
(C3-C6)-cycloalkylsulfinyl, (C1-C4)-alkylsulfonyl,
(C3-C6)-cyclo-alkyl-sul-fo-nyl,
(C1-C4)-alkylsulfonyloxy,
(C3-C6)-cycloalkylsulfonyloxy, (C2-C3)-alkenyl,
(C2-C3)-alkynyl, (C2-C3)-alkenyloxy,
(C2-C3)-alkynyloxy, --NHCO--(C1-C3)-alkyl,
--NHCO2--(C1-C3)-alkyl, --NHCONH--(C1-C3)-alkyl,
--NHSO2--(C1-C3)-alkyl, --NHCONH--(C1-C3)-alkyl,
--CONHR9, --CONR9R10, where R9 and R10
independently of one another selected from the group consisting of
hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl and
(C1-C6)-haloalkyl; and where the radical R2 may be mono-
or polysubstituted by radicals selected from the group consisting of
halogen and (C1-C6)-alkyl.

4. A compound of the formula (I), its agrochemically acceptable salt or
its agrochemically acceptable quaternized nitrogen derivative as claimed
in claim 1, wherein the radical R3 is selected from the group
consisting of hydrogen, hydroxyl, halogen, cyano, nitro, amino, C(O)OH,
(C1-C4)-alkyl, (C3-C6)-cycloalkyl,
(C1-C4)-haloalkyl, (C1-C4)-alkoxy,
(C1-C4)-haloalkoxy,
(C1-C4)-alkoxy-(C1-C2)-alkyl,
(C1-C3)-alkylcarbonyl, (C1-C3)-alkylcarbonyloxy,
(C1-C4)-alkoxycarbonyl, (C3-C6)-cycloalkoxycarbonyl,
(C3-C6)-cycloalkyl-(C1-C2)-alkoxy,
(C3-C6)-cycloalkoxy,
(C1-C4)-alkoxycarbonyl-(C1-C2)-alkoxy,
(C3-C4)-alkenyl-oxy, (C3-C4)-alkynyloxy,
(C1-C4)-alkylthio, (C1-C4)-haloalkylthio,
(C1-C4)-alkylsulfinyl, (C1-C4)-haloalkylsulfinyl,
(C1-C4)-alkylsulfonyl, (C1-C4)-haloalkylsulfonyl,
(C1-C4)-alkylsulfonyloxy, di-(C1-C4)-alkylamino,
(C3-C4)-alkenyloxycarbonyl,
(C2-C4)-alkynyloxycarbonyl, formyl, (C2-C4)-alkenyl,
(C2-C4)-alkynyl, --C(O)NR9R10, where R9 and
R10 are independently of one another selected from the group
consisting of hydrogen, (C1-C6)-alkyl,
(C3-C6)-cycloalkyl, (C1-C6)-haloalkyl, or where
R9 and R10 together form a (C1-C6)-alkylene group
which may contain an oxygen or sulfur atom or one or two amino or
(C1-C6)-alkylamino groups.

5. A compound of the formula (I), its agrochemically acceptable salt or
its agrochemically acceptable quaternized nitrogen derivative as claimed
in claim 1, wherein the radical R4 is selected from the group
consisting of hydrogen, hydroxyl, halogen, cyano, nitro, amino, C(O)OH,
(C1-C4)-alkyl, (C3-C6)-cycloalkyl,
(C1-C4)-haloalkyl, (C1-C4)-alkoxy,
(C1-C4)-haloalkoxy,
(C1-C4)-alkoxy-(C1-C2)-alkyl,
(C1-C3)-alkylcarbonyl, (C1-C3)-alkylcarbonyloxy,
(C1-C4)-alkoxycarbonyl, (C3-C6)-cycloalkoxycarbonyl,
(C3-C6)-cycloalkyl-(C1-C2)-alkoxy,
(C3-C6)-cycloalkoxy,
(C1-C4)-alkoxycarbonyl-(C1-C2)-alkoxy,
(C3-C4)-alkenyl-oxy, (C3-C4)-alkynyloxy,
(C1-C4)-alkylthio, (C1-C4)-haloalkylthio,
(C1-C4)-alkylsulfinyl, (C1-C4)-haloalkylsulfinyl,
(C1-C4)-alkylsulfonyl, (C1-C4)-haloalkylsulfonyl,
(C1-C4)-alkylsulfonyloxy, di-(C1-C4)-alkylamino,
(C3-C4)-alkenyloxycarbonyl,
(C2-C4)-alkynyloxycarbonyl, formyl, (C2-C4)-alkenyl,
(C2-C4)-alkynyl, --C(O)NR9R10, where R9 and
R10 are independently of one another selected from the group
consisting of hydrogen, (C1-C6)-alkyl,
(C3-C6)-cycloalkyl, (C1-C6)-haloalkyl, or where
R9 and R10 together form a (C1-C6)-alkylene group
which may contain an oxygen or sulfur atom or one or two amino or
(C--C)-alkylamino groups.

6. A compound of the formula (I), its agrochemically acceptable salt or
its agrochemically acceptable quaternized nitrogen derivative as claimed
in claim 1, wherein the radical R is selected from the group consisting
of hydrogen, hydroxyl, halogen, cyano, nitro, amino, C(O)OH,
(C1-C4)-alkyl, (C3-C6)-cycloalkyl,
(C1-C4)-alkoxy, (C1-C4)-haloalkoxy,
(C1-C4)-alkoxy-(C1-C2)-alkyl,
(C1-C3)-alkylcarbonyl, (C1-C3)-alkylcarbonyloxy,
(C1-C4)-alkoxycarbonyl, (C3-C6)-cycloalkoxycarbonyl,
(C3-C6)-cycloalkyl-(C1-C2)-alkoxy,
(C3-C6)-cycloalkoxy,
(C1-C4)-alkoxycarbonyl-(C1-C2)-alkoxy,
(C3-C4)-alkenyl-oxy, (C3-C4)-alkynyloxy,
(C1-C4)-alkylthio, (C1-C4)-haloalkylthio,
(C1-C4)-alkylsulfinyl, (C1-C4)-haloalkylsulfinyl,
(C1-C4)-alkylsulfonyl, (C1-C4)-haloalkylsulfonyl,
(C1-C4)-alkylsulfonyloxy, di-(C1-C4)-alkylamino,
(C3-C4)-alkenyloxycarbonyl,
(C2-C4)-alkynyloxycarbonyl, formyl, (C2-C4)-alkenyl,
(C2-C4)-alkynyl, --C(O)NR9R10, where R9 and
R10 independently of one another selected from the group consisting
of hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl,
(C1-C6)-haloalkyl, or where R9 and R10 together form
a (C1-C6)-alkylene group which may contain an oxygen or sulfur
atom or one or two amino or (C1-C6)-alkylamino groups.

7. A compound of the formula (I), its agrochemically acceptable salt or
its agrochemically acceptable quaternized nitrogen derivative as claimed
in claim 1, wherein the radical R6 is selected from the group
consisting of hydrogen, hydroxyl, halogen, cyano, nitro, amino, C(O)OH,
(C1-C4)-alkyl, (C3-C6)-cycloalkyl,
(C1-C4)-haloalkyl, (C1-C4)-alkoxy,
(C1-C4)-haloalkoxy,
(C1-C4)-alkoxy-(C1-C2)-alkyl,
(C1-C3)-alkylcarbonyl, (C1-C3)-alkylcarbonyloxy,
(C1-C4)-alkoxycarbonyl, (C3-C6)-cycloalkoxycarbonyl,
(C3-C6)-cycloalkyl-(C1-C2)-alkoxy,
(C3-C6)-cycloalkoxy,
(C1-C4)-alkoxycarbonyl-(C1-C2)-alkoxy,
(C3-C4)-alkenyloxy, (C3-C4)-alkynyloxy,
(C1-C4)-alkylthio, (C1-C4)-haloalkylthio,
(C1-C4)-alkylsulfinyl, (C1-C4)-haloalkylsulfinyl,
(C1-C4)-alkylsulfonyl, (C1-C4)-haloalkylsulfonyl,
(C1-C4)-alkylsulfonyloxy, di-(C1-C4)-alkylamino,
(C3-C4)-alkenyloxycarbonyl,
(C2-C4)-alkynyloxycarbonyl, formyl, (C2-C4)-alkenyl,
(C2-C4)-alkynyl, --C(O)NR9R10 where R9 and
R10 are independently of one another selected from the group
consisting of hydrogen, (C1-C6)-alkyl,
(C3-C6)-cycloalkyl, (C1-C6)-haloalkyl, or where
R9 and R10 together form a (C1-C6)-alkylene group
which may contain an oxygen or sulfur atom or one or two amino or
(C1-C6)-alkylamino groups.

8. A compound of the formula (I), its agrochemically acceptable salt or
its agrochemically acceptable quaternized nitrogen derivative as claimed
in claim 1, wherein the radical R7 is selected from the group
consisting of hydrogen, hydroxyl, halogen, cyano, nitro, amino, C(O)OH,
(C1-C4)-alkyl, (C3-C6)-cycloalkyl,
(C1-C4)-haloalkyl, (C1-C4)-alkoxy,
(C1-C4)-haloalkoxy,
(C1-C4)-alkoxy-(C1-C2)-al-kyl,
(C1-C3)-alkylcarbonyl, (C1-C3)-alkylcarbonyloxy,
(C1-C4)-alkoxycarbonyl, (C3-C6)-cycloalkoxycarbonyl,
(C3-C6)-cycloalkyl-(C1-C2)-alkoxy,
(C3-C6)-cycloalkoxy,
(C1-C4)-alkoxycarbonyl-(C1-C2)-alkoxy,
(C3-C4)-alkenyl-oxy, (C3-C4)-alkynyloxy,
(C1-C4)-alkylthio, (C1-C4)-haloalkylthio,
(C1-C4)-alkylsulfinyl, (C1-C4)-haloalkylsulfinyl,
(C1-C4)-alkylsulfonyl, (C1-C4)-haloalkylsulfonyl,
(C1-C4)-alkylsulfonyloxy, di-(C1-C4)-alkylamino,
(C3-C4)-alkenyloxycarbonyl,
(C2-C4)-alkynyloxycarbonyl, formyl, (C2-C4)-alkenyl,
(C2-C4)-alkynyl, --C(O)NR9R10, where R9 and
R10 are independently of one another selected from the group
consisting of hydrogen, (C1-C6)-alkyl,
(C3-C6)-cycloalkyl, (C1-C6)-haloalkyl, or where
R9 and R10 together form a (C1-C6)-alkylene group
which may contain an oxygen or sulfur atom or one or two amino or
(C1-C6)-alkylamino groups.

9. A compound as claimed in claim 1, wherein n is 1.

10. A compound as claimed in claim 9, wherein the compound of the formula
(I) where n=1 is present in the (R) or (S) configuration in a
stereochemical purity of more than 50% to 100%.

11. A process for preparing a compound of the formula (III) or a compound
of the formula (IV), wherein R1, R2, R3, R4, R5,
R6, R7 have the meanings given above for formula (I),
##STR00045## which comprises oxidizing a thioether of the formula (II),
##STR00046## wherein R1, R2, R3, R4, R5,
R6, R7 have the meanings given above for formula (I), with one
equivalent of an oxidizing agent to give the optically active sulfoxides
(III) for which n is the number 1, or with two equivalents of an
oxidizing agent to give the sulfones (IV) for which n is the number 2.

12. A process for preparing a thioether of the formula (II) ##STR00047##
in which R1, R2, R3, R4, R5, R6 and
R7 have the meanings given in claim 1 any of claims 1 to 8,
according to one of the processes below: (a) reaction of
2-mercaptooxazole or an oxazole-2(3H)-thione or a salt thereof
##STR00048## in which R1, R2 have the meanings given in claim
1, with a benzyl derivative of the formula (VI) ##STR00049## in which
R3, R4, R5, R6, R7 have the meanings given above
for formula (I) and Lg is a leaving group, in the presence of an alkali
metal or alkaline earth metal base or an organic base in a solvent; (b)
reaction of an oxazole derivative of the formula (VII), ##STR00050## in
which R1, R2 have the meanings given in claim 1 and Lg' is a
leaving group with a benzyl imidothiocarbamate salt of the formula (VIII)
##STR00051## in which R3, R4, R5, R6, R7 have
the meanings given above for formula (I), Lg is a leaving group, in a
one-pot process in the presence of an aqueous alkali metal or alkaline
earth metal base or an alkali metal or alkaline earth metal carbonate
base and a solvent; (c) reaction of an oxazole derivative of the formula
(VII), ##STR00052## in which R1, R2 have the meanings given
above for formula (I) and Lg' is a leaving group with a benzyl
imidothiocarbamate salt (isothiuronium salt) of the formula (VIII)
##STR00053## in which R3, R4, R5, R6, R7 have
the meanings given above for formula (I), Lg is a leaving group, in a
one-pot process in the presence of an alkali metal or alkaline earth
metal carbonate base and a solvent; (d) reaction of an oxazole derivative
of the formula (VII), ##STR00054## in which R1, R2 have the
meanings given above for formula (I) and Lg' is a leaving group with a
benzyl mercaptan of the formula (IX), ##STR00055## in which R3,
R4, R5, R6, R7 have the meanings given above for
formula (I) in the presence of an alkali metal or alkaline earth metal
base or organic base, optionally in a solvent; (e) reaction of an oxazole
derivative of the formula (X), ##STR00056## in which R2, R3,
R4, R5, R6, R7 have the meanings given above for
formula (I), according to the formula scheme below: ##STR00057## where
the compounds of the formula (X) are treated with a halogenating agent or
with a nitrating agent and are reacted in suitable solvents to give
compounds of the formula (II); (f) reaction of an oxazole derivative of
the formula (XI), ##STR00058## prepared from an oxazole derivative of
the formula (V), by reaction with an alkylating agent R12Lg' in
which R2 has the meanings given above for formula (I), R12 is
preferably (C1-C6)-alkyl which is unsubstituted or substituted
by one or more identical or different radicals from the halogen group and
Lg' is a leaving group, with a strong base and an alkylating agent
R1Lg' in which R1 has the meanings given above for formula (I),
according to the scheme ##STR00059## in which R1, R2,
R3, R4, R5, R6, R7 have the meanings given above
for formula (I) and Lg or Lg' is a leaving group; (g) reaction of a
benzyl disulfide derivative of the formula (XV) with 2-amino-oxazoles of
the formula (XIV) and a diazotizing agent as shown in the scheme below,
##STR00060## in which R1, R2, R3, R4, have the
meanings given above for formula (I).

13. The process as claimed in claim 11 wherein the compound of the
formula (II) obtained by the process as claimed in claim 12 is used as
starting material in the process as claimed in claim 11.

14. A composition comprising at least one compound of the formula (I)
according to claim 1.

15. The composition as claimed in claim 14 wherein the composition
comprises at least one further active compound selected from the group
consisting of at least one further herbicide and at least one safener.

16. A method of regulating plant growth which comprises administering an
effective amount of the compound of formula (I) according to claim 1.

17. The method of claim 16 wherein the regulation of plant growth occurs
within a specific crop plant.

18. The compound of claim 2, wherein wherein the radical R2 is
selected from the group consisting of hydrogen, halogen, nitro, cyano,
carboxyl, (C1-C6)-alkyl, (C3-C6)-cycloalkyl,
(C3-C6)-cycloalkoxy, (C1-C6)-alkoxy,
(C1-C6)-alkylcarbonyl, (C3-C6)-cycloalkylcarbonyl,
(C1-C6)-alkoxycarbonyl, (C3-C6)-cycloalkoxycarbonyl,
mono-((C1-C4)-alkyl)aminocarbonyl,
di-((C1-C4)-alkyl)aminocarbonyl,
mono-((C1-C4)-alkyl)aminosulfonyl,
di-((C1-C4)-alkyl)aminosulfonyl, (C1-C4)-alkyl-thio,
(C3-C6)-cycloalkylthio, (C1-C4)-alkylsulfinyl,
(C3-C6)-cycloalkylsulfinyl, (C1-C4)-alkylsulfonyl,
(C3-C6)-cyclo-alkyl-sul-fo-nyl,
(C1-C4)-alkylsulfonyloxy,
(C3-C6)-cycloalkylsulfonyloxy, (C2-C3)-alkenyl,
(C2-C3)-alkynyl, (C2-C3)-alkenyloxy,
(C2-C3)-alkynyloxy, --NHCO--(C1-C3)-alkyl,
--NHCO2--(C1-C3)-alkyl, --NHCONH--(C1-C3)-alkyl,
--NHSO2--(C1-C3)-alkyl, --OCONH--(C1-C3)-alkyl,
--CONHR9, --CONR9R10, where R9 and R10 are
independently of one another selected from the group consisting of
hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl and
(C1-C6)-haloalkyl; and where the radical R2 may be mono-
or polysubstituted by radicals selected from the group consisting of
halogen and (C1-C6)-alkyl; wherein the radical R3 is
selected from the group consisting of hydrogen, hydroxyl, halogen, cyano,
nitro, amino, C(O)OH, (C1-C4)-alkyl,
(C3-C6)-cycloalkyl, (C1-C4)-haloalkyl,
(C1-C4)-alkoxy, (C1-C4)-haloalkoxy,
(C1-C4)-alkoxy-(C1-C2)-alkyl,
(C1-C3)-alkylcarbonyl, (C1-C3)-alkylcarbonyloxy,
(C1-C4)-alkoxycarbonyl, (C3-C6)-cyclo alkoxycarbonyl,
(C3-C6)-cycloalkyl-(C1-C2)-alkoxy,
(C3-C6)-cycloalkoxy,
(C1-C4)-alkoxycarbonyl-(C1-C2)-alkoxy,
(C3-C4)-alkenyl-oxy, (C3-C4)-alkynyloxy,
(C1-C4)-alkylthio, (C1-C4)-haloalkylthio,
(C1-C4)-alkylsulfinyl, (C1-C4)-haloalkylsulfinyl,
(C1-C4)-alkylsulfonyl, (C--C)-haloalkylsulfonyl,
(C1-C4)-alkylsulfonyloxy, di-(C1-C4)-alkylamino,
(C3-C4)-alkenyloxycarbonyl,
(C2-C4)-alkynyloxycarbonyl, formyl, (C2-C4)-alkenyl,
(C2-C4)-alkynyl, --C(O)NR9R10, where R9 and
R10 are independently of one another selected from the group
consisting of hydrogen, (C1-C6)-alkyl,
(C3-C6)-cycloalkyl, (C1-C6)-haloalkyl, or where
R9 and R10) together form a (C1-C6)-alkylene group
which may contain an oxygen or sulfur atom or one or two amino or
(C1-C6)-alkylamino groups; wherein the radical R4 is
selected from the group consisting of hydrogen, hydroxyl, halogen, cyano,
nitro, amino, C(O)OH, (C1-C4)-alkyl,
(C3-C6)-cycloalkyl, (C1-C4)-haloalkyl,
(C1-C4)-alkoxy, (C1-C4)-haloalkoxy,
(C1-C4)-alkoxy-(C1-C2)-alkyl,
(C1-C3)-alkylcarbonyl, (C1-C3)-alkylcarbonyloxy,
(C1-C4)-alkoxycarbonyl, (C3-C6)-cycloalkoxycarbonyl,
(C3-C6)-cycloalkyl-(C1-C2)-alkoxy,
(C3-C6)-cycloalkoxy,
(C1-C4)-alkoxycarbonyl-(C1-C2)-alkoxy,
(C3-C4)-alkenyl-oxy, (C3-C4)-alkynyloxy,
(C1-C4)-alkylthio, (C1-C4)-haloalkylthio,
(C1-C4)-alkylsulfinyl, (C1-C4)-haloalkylsulfinyl,
(C1-C4)-alkylsulfonyl, (C1-C4)-haloalkylsulfonyl,
(C1-C4)-alkylsulfonyloxy, di-(C1-C4)-alkylamino,
(C3-C4)-alkenyloxycarbonyl,
(C2-C4)-alkynyloxycarbonyl, formyl, (C2-C4)-alkenyl,
(C2-C4)-alkynyl, --C(O)NR9R10, where R9 and
R10 are independently of one another selected from the group
consisting of hydrogen, (C1-C6)-alkyl,
(C3-C6)-cycloalkyl, (C1-C6)-haloalkyl, or where
R9 and R10 together form a (C1-C6)-alkylene group
which may contain an oxygen or sulfur atom or one or two amino or
(C1-C6)-alkylamino groups; wherein the radical R5 is
selected from the group consisting of hydrogen, hydroxyl, halogen, cyano,
nitro, amino, C(O)OH, (C1-C4)-alkyl,
(C3-C6)-cycloalkyl, (C1-C4)-haloalkyl,
(C1-C4)-alkoxy, (C1-C4)-haloalkoxy,
(C1-C4)-alkoxy-(C1-C2)-alkyl,
(C1-C3)-alkylcarbonyl, (C1-C3)-alkylcarbonyloxy,
(C1-C4)-alkoxycarbonyl, (C3-C6)-cycloalkoxycarbonyl,
(C3-C6)-cycloalkyl-(C1-C2)-alkoxy,
(C3-C6)-cycloalkoxy,
(C1-C4)-alkoxycarbonyl-(C1-C2)-alkoxy,
(C3-C4)-alkenyl-oxy, (C3-C4)-alkynyloxy,
(C1-C4)-alkylthio, (C1-C4)-haloalkylthio,
(C1-C4)-alkylsultinyl, (C1-C4)-haloalkylsulfinyl,
(C1-C4)-alkylsulfonyl, (C1-C4)-haloalkylsulfonyl,
(C1-C4)-alkylsulfonyloxy, di-(C1-C4)-alkylamino,
(C3-C4)-alkenyloxycarbonyl,
(C2-C4)-alkynyloxycarbonyl, formyl, (C2-C4)-alkenyl,
(C2-C4)-alkynyl, --C(O)NR9R10, where R9 and
R10 are independently of one another selected from the group
consisting of hydrogen, (C1-C6)-alkyl,
(C3-C6)-cycloalkyl, (C1-C6)-haloalkyl, or where
R9 and R10 together form a (C1-C6)-alkylene group
which may contain an oxygen or sulfur atom or one or two amino or
(C1-C6)-alkylamino groups; wherein the radical R6 is
selected from the group consisting of hydrogen, hydroxyl, halogen, cyano,
nitro, amino, C(O)OH, (C1-C4)-alkyl,
(C3-C6)-cycloalkyl, (C1-C4)-haloalkyl,
(C1-C4)-alkoxy, (C1-C4)-haloalkoxy,
(C1-C4)-alkoxy-(C1-C2)-alkyl,
(C1-C3)-alkylcarbonyl, (C1-C3)-alkylcarbonyloxy,
(C1-C4)-alkoxycarbonyl, (C3-C6)-cycloalkoxycarbonyl,
(C3-C6)-cycloalkyl-(C1-C2)-alkoxy,
(C3-C6)-cycloalkoxy,
(C1-C4)-alkoxycarbonyl-(C1-C2)-alkoxy,
(C3-C4)-alkenyloxy, (C3-C4)-alkynyloxy,
(C1-C4)-alkylthio, (C1-C4)-haloalkylthio,
(C1-C4)-alkylsulfinyl, (C1-C4)-haloalkylsulfinyl,
(C1-C4)-alkylsulfonyl, (C1-C4)-haloalkylsulfonyl,
(C1-C4)-alkylsulfonyloxy, di-(C1-C4)-alkylamino,
(C3-C4)-alkenyloxycarbonyl,
(C2-C4)-alkynyloxycarbonyl, formyl, (C2-C4)-alkenyl,
(C2-C4)-alkynyl, --C(O)NR9R10, where R9 and
R10 are independently of one another selected from the group
consisting of hydrogen, (C1-C6)-alkyl,
(C3-C6)-cycloalkyl, (C1-C6)-haloalkyl, or where
R9 and R10 together form a (C1-C6)-alkylene group
which may contain an oxygen or sulfur atom or one or two amino or
(C1-C6)-alkylamino groups; and wherein the radical R7 is
selected from the group consisting of hydrogen, hydroxyl, halogen, cyano,
nitro, amino, C(O)OH, (C1-C4)-alkyl,
(C3-C6)-cycloalkyl, (C1-C4)-haloalkyl,
(C1-C4)-alkoxy, (C1-C4)-haloalkoxy,
(C1-C4)-alkoxy-(C1-C2)-al-kyl,
(C1-C3)-alkylcarbonyl, (C1-C3)-alkylcarbonyloxy,
(C1-C4)-alkoxycarbonyl, (C3-C6)-cycloalkoxycarbonyl,
(C3-C6)-cycloalkyl-(C1-C2)-alkoxy,
(C3-C6)-cycloalkoxy,
(C1-C4)-alkoxycarbonyl-(C1-C2)-alkoxy,
(C3-C4)-alkenyl-oxy, (C3-C4)-alkynyloxy,
(C1-C4)-alkylthio, (C1-C4)-haloalkylthio,
(C1-C4)-alkylsulfinyl, (C1-C4)-haloalkylsulfinyl,
(C1-C4)-alkylsulfonyl, (C1-C4)-haloalkylsulfonyl,
(C1-C4)-alkylsulfonyloxy, di-(C1-C4)-alkylamino,
(C3-C4)-alkenyloxycarbonyl,
(C2-C4)-alkynyloxycarbonyl, formyl, (C2-C4)-alkenyl,
(C2-C4)-alkynyl, --C(O)NR9R10, where R9 and
R10 are independently of one another selected from the group
consisting of hydrogen, (C1-C6)-alkyl,
(C3-C6)-cycloalkyl, (C1-C6)-haloalkyl, or where
R9 and R10 together form a (C1-C6)-alkylene group
which may contain an oxygen or sulfur atom or one or two amino or
(C1-C6)-alkylamino groups.

Description:

[0001] The present invention relates to specific compounds selected from
the group of the 2-(benzylsulfonyl)oxazole derivatives, chiral
2-(benzylsulfinyl)oxazole derivatives, and 2-(benzylsulfanyl)oxazole
derivatives, and to specific processes for their preparation. The present
invention furthermore provides the use of these compounds as herbicides,
in particular as herbicides for the selective control of harmful plants
in crops of useful plants. Furthermore, the present invention relates to
their use as plant growth regulators on their own or in combination with
safeners and/or as a mixture with other herbicides, to their use in the
control of plants in specific crop plants or as plant protection
regulators.

[0002] It is already known from various publications that certain oxazole
derivatives have herbicidal properties.

[0003] Thus, WO 2004/013112 A describes herbicidally active oxazole
derivatives which have a fluoroalkene-containing thioether group at the
2-position of the oxazole ring.

[0004] U.S. Pat. No. 4,022,607 describes 2-(alkylsulfinyl)oxazole
derivatives, their preparation and their use as herbicides.

[0005] DE 102 54 876 A describes 2-(fluoroalkenylthio)oxazole compounds
and their use as herbicides.

[0006] EP 0 435 794 A describes 1-heterocyclylsulfonyl-2-phenyl-2-propenes
and their use as herbicides.

[0008] 2-[(1H-Pyrazol-4-ylmethyl)sulfinyl] and
2-[(1H-pyrazol-4-ylmethyl)sulfonyl] derivatives having herbicidal
properties have also been described. Thus, WO 2007/071900 A, WO 02/62770
A and WO 2006/123088 describe a number of 2-[(1H-pyrazol-4-10
ylmethyl)sulfinyl] and 2-[(1H-pyrazol-4-ylmethyl)sulfonyl] derivatives
which carry a suitable substituted (1H-pyrazol-4-ylmethyl) group as
substituent at the 2-sulfonyl or 2-sulfinyl group. The publications
mentioned above also describe a process for their preparation.

[0009] 2-(Arylmethylsulfonyl)-substituted derivatives having herbicidal
properties have also been described. Thus, JP 2003/096059 A and WO
01/112613 A and U.S. Pat. No. 3,960,542 describe a number of
2-(arylmethylsulfonyl) derivatives having a suitable substituted
phenylmethyl group as substituent at the 2-sulfonyl group. The
publications mentioned above also describe a process for their
preparation.

[0010] However, the active compounds already known from the publications
mentioned above, when used as herbicides, have disadvantages, be it (a)
that they have insufficient, if any, herbicidal activity against harmful
plants, (b) that the spectrum of harmful plants which can be controlled
by one active compound is not wide enough, or (c) that their selectivity
in crops of useful plants is too low.

[0011] For these reasons, it is desirable to provide alternative chemical
active compounds which can be employed as herbicides or plant growth
regulators, if appropriate with further advantages.

[0012] Benzodioxazole derivatives suitable for the treatment of liver
disorders are known in the field of medicine JP 620 39 583 A.

[0013] The present invention now provides 2-(benzylsulfonyl)oxazole
derivatives, 2-(benzylsulfanyl)oxazole derivatives and chiral
2-(benzylsulfinyl)oxazole derivatives which have advantages compared to
the compounds described in the prior art.

in which [0015] n is 0, 1, 2; [0016] the substituents R1 and
R2 are each independently of one another selected from the group
consisting of [0017] hydrogen, halogen, nitro, cyano, formyl, --C(O)OH,
hydroxyl, and amino; [0018] (C1-C6)-alkyl,
(C1-C6)-alkylcarbonyl,
(C1-C6)-alkylcarbonyl-(C1-C4)-alkyl and
(C1-C6)-alkylcarbonyloxy; [0019] (C1-C6)-alkoxy,
(C1-C6)-alkoxycarbonyl,
(C1-C6)-alkoxycarbonyl-(C1-C6)-alkyl,
(C1-C6)-alkoxy-(C1-C6)-alkyl,
(C1-C6)-alkoxy-(C1-C6)-alkoxy and
(C1-C6)-alkoxycarbonyl-(C1-C6)-alkoxy; [0020]
(C2-C6)-alkenyl, (C2-C6)-alkenyloxy,
(C2-C6)-alkynyl and (C2-C6)-alkynyloxy; [0021]
(C1-C6)-alkylthio, (C1-C6)-alkylsulfinyl,
(C1-C6)-alkylsulfonyl, (C1-C6)-alkylsulfonyloxy,
(C1-C6)-alkylsulfonyl-(C1-C6)-alkyl,
(C1-C6)-alkylsulfinyl-(C1-C6)-alkyl,
(C1-C6)-alkylthio-(C1-C6)-alkyl and
(C1-C6)-alkylthio-(C1-C6)-alkoxY; [0022]
mono-((C1-C6)-alkyl)amino, di-((C1-C6)-alkyl)amino,
N--((C1-C6)-alkanoyl)amino,
aminocarbonyl-(C1-C6)-alkyl,
mono-((C1-C6)-alkyl)aminocarbonyl,
di-((C1-C6)-alkyl)aminocarbonyl,
mono-((C1-C6)-alkyl)aminosulfonyl and
di-((C1-C6)-alkyl)aminosulfonyl; [0023]
(C3-C8)-cycloalkyl, (C3-C8)-cycloalkoxy,
(C3-C8)-cycloalkyl-(C1-C6)-alkyl,
(C3-C8)-cycloalkyl-(C1-C6)-alkoxy,
(C3-C8)-cycloalkylcarbonyl and
(C3-C8)-cycloalkoxycarbonyl; [0024]
(C3-C8)-cycloalkenyl, (C3-C8)-cycloalkenyloxy,
(C3-C8)-cycloalkylthio, [0025]
(C3-C8)-cycloalkylsulfinyl,
(C3-C8)-cycloalkylsulfonyl and
(C3-C8)-cycloalkylsulfonyloxy; [0026]
cyano-(C1-C6)-alkoxy and cyano-(C1-C6)-alkyl; [0027]
--CONN--SO2--(C1-C6)-alkyl, --NHCHO,
--NHCO--(C1-C6)-alkyl, --NHCO2--(C1-C6)-alkyl,
--NHCONH--(C1-C6)-alkyl, --NHSO2--(C1-C6)-alkyl,
--OCONH--(C1-C6)-alkyl,
(C1-C6)-alkylaminosulfonyl-(C1-C2)-alkyl,
di-(C1-C6)-alkylaminosulfonyl-(C1-C2)-alkyl,
--C(O)NHR9, --C(O)NR9R10, where R9 and R10 are
each independently of one another selected from the group consisting of
hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl,
(C1-C6)-haloalkyl, or where R9 and R10 together form
a (C1-C6)-alkylene group which may contain an oxygen or a
sulfur atom or one or two amino or (C1-C6)-alkylamino groups,
[0028] the substituents R3 to R7 are each independently of one
another selected from the group consisting of [0029] hydrogen, halogen,
hydroxyl, cyano, nitro, amino, C(O)OH and formyl; [0030]
(C1-C6)-alkyl, (C1-C6)-haloalkyl,
(C1-C6)-alkylcarbonyl, (C1-C6)-haloalkylcarbonyl,
(C1-C6)-alkylcarbonyloxy,
(C1-C6)-halo-alkylcarbonyloxy,
(C1-C6)-alkylcarbonyl-(C1-C4)-alkyl,
(C1-C6)-haloalkylcarbonyl-(C1-C4)-alkyl,
(C1-C6)-alkylcarbonyl-(C1-C4)-haloalkyl and
(C1-C6)-haloalkylcarbonyl-(C1-C4)-haloalkyl; [0031]
(C1-C6)-alkoxy, (C1-C6)-haloalkoxy,
(C1-C6)-alkoxycarbonyl, (C1-C6)-haloalkoxycarbonyl,
(C1-C6)-alkoxycarbonyl-(C1-C6)-alkyl,
(C1-C6)-haloalkoxycarbonyl-(C1-C6)-alkyl,
(C1-C6)-alkoxycarbonyl-(C1-C6)-haloalkyl and
(C1-C6)-haloalkoxycarbonyl-(C1-C6)-haloalkyl; [0032]
(C2-C6)-alkenyl, (C2-C6)-haloalkenyl,
(C2-C6)-alkenylcarbonyl, (C2-C6)-haloalkenylcarbonyl,
(C2-C6)-alkenyloxy, (C2-C6)-halo-alkenyloxy,
(C2-C6)-alkenyloxycarbonyl and
(C2-C6)-haloalkenyl-oxycarbonyl; [0033]
(C2-C6)-alkynyl, (C2-C6)-haloalkynyl,
(C2-C6)-alkynylcarbonyl, (C2-C6)-haloalkynylcarbonyl,
(C2-C6)-alkynyloxy, (C2-C6)-haloalkynyl-oxy,
(C2-C6)-alkynyloxycarbonyl and
(C2-C6)-haloalkynyloxycarbonyl; [0034]
(C1-C6)-alkylthiocarbonyl,
(C1-C6)-haloalkylthiocarbonyl,
(C1-C6)-alkylthiocarbonyloxy and
(C1-C6)-haloalkylthiocarbonyloxy; [0035]
(C1-C6)-alkylthio-(C1-C6)-alkoxy,
(C1-C6)-alkylthio-(C1-C6)-alkylcarbony) and
(C1-C6)-alkylthio-(C1-C6)-alkylcarbonyloxy; [0036]
(C1-C6)-alkylsulfonyl, (C1-C6)-alkylthio,
(C1-C6)-alkylsulfinyl, (C1-C6)-haloalkylsulfonyl,
(C1-C6)-haloalkylthio, (C1-C6)-halo-alkylsulfinyl,
(C1-C6)-alkylsulfonyl-(C1-C6)-alkyl,
(C1-C6)-alkylthio-(C1-C6)-alkyl,
(C1-C6)-alkylsulfinyl-(C1-C6)-alkyl,
(C1-C6)-haloalkylsulfonyl-(C1-C6)-alkyl,
(C1-C6)-haloalkylthio-(C1-C6)-alkyl,
(C1-C6)-haloalkylsulfinyl-(C1-C6)-alkyl,
(C1-C6)-alkylsulfonyl-(C1-C6)-haloalkyl,
(C1-C6)-alkylthio-(C1-C6)-haloalkyl,
(C1-C6)-alkylsulfinyl-(C1-C6)-haloalkyl,
(C1-C6)-haloalkylsulfonyl-(C1-C6)-haloalkyl,
(C1-C6)-haloalkylthio-(C1-C6)-haloalkyl,
(C1-C6)-haloalkylsulfinyl-(C1-C6)-haloalkyl,
(C1-C6)-alkylsulfonyloxy and
(C1-C6)-haloalkylsulfonyloxy; [0037]
mono-((C1-C6)-alkyl)amino,
mono-((C1-C6)-haloalkyl)amino,
di-((C1-C6)-alkyl)amino, di-((C1-C6)-haloalkyl)amino,
((C1-C6)-alkyl-(C1-C6)-haloalkyl)amino,
N--((C1-C6)-alkanoyl)amino,
N--((C1-C6)-haloalkanoyl)amino,
aminocarbonyl-(C1-C6)-alkyl,
mono-(C1-C6)-alkylaminocarbonyl-(C1-C6)-alkyl,
di-(C1-C6)-alkylaminocarbonyl-(C1-C6)-alkyl and
mono-((C1-C6)-alkyl)aminocarbonyl; [0038]
(C1-C6)-alkoxy-(C1-C6)-alkyl,
(C1-C6)-alkoxy-(C1-C6)-alkoxy,
(C1-C6)-alkoxycarbonyl-(C1-C6)-alkoxy, [0039]
(C3-C8)-cycloalkyl, (C3-C8)-cycloalkoxy,
(C3-C8)-cycloalkyl-(C1-C6)-alkyl,
(C3-C8)-cycloalkyl-(C1-C6)-haloalkyl,
(C3-C8)-cycloalkyl-(C1-C6)-alkoxy,
(C3-C8)-cycloalkyl-(C1-C6)-haloalkoxy,
(C3-C8)-cycloalkylcarbonyl,
(C3-C8)-cycloalkoxycarbonyl,
(C3-C8)-cycloalkyl-(C1-C6)-alkylcarbonyl,
(C3-C8)-cycloalkyl-(C1-C6)-halo-alkylcarbonyl,
(C3-C8)-cycloalkyl-(C1-C6)-alkoxycarbonyl,
(C3-C8)-cycloalkyl-(C1-C6)-haloalkoxycarbonyl,
(C3-C8)-cycloalkylcarbonyl-oxy,
(C3-C8)-cycloalkoxycarbonyloxy,
(C3-C8)-cycloalkyl-(C1-C6)-alkylcarbonyloxy,
(C3-C8)-cycloalkyl-(C1-C6)-haloalkylcarbonyloxy,
(C3-C8)-cycloalkyl-(C1-C6)-alkoxycarbonyloxy and
(C3-C8)-cycloalkyl-(C1-C6)-haloalkoxycarbonyloxy;
[0040] (C3-C8)-cycloalkenyl, (C3-C8)-cycloalkenyloxy,
(C3-C8)-cycloalke-nyl-(C1-C6)-alkyl,
(C3-C8)-cycloalkenyl-(C1-C6)-haloalkyl,
(C3-C8)-cycloalkenyl-(C1-C6)-alkoxy,
(C3-C8)-cycloalkenyl-(C1-C6)-haloalkoxy,
(C3-Cs)-cycloalkenylcarbonyl,
(C3-C8)-cycloalkenyloxycarbonyl,
(C3-C8)-cycloalkenyl-(C1-C6)-alkylcarbonyl,
(C3-C8)-cycloalkenyl-(C1-C6)-haloalkylcarbonyl,
(C3-C8)-cycloalkenyl-(C1-C6)-alkoxycarbonyl,
(C3-C8)-cycloalkenyl-(C1-C6)-ha-loalkoxycarbonyl,
(C3-C8)-cycloalkenylcarbonyloxy,
(C3-C8)-cyclo-alkenyloxycarbonyloxy,
(C3-C8)-cycloalkenyl-(C1-C6)-alkylcar-bonyloxy,
(C3-C8)-cycloalkenyl-(C1-C6)-haloalkylcarbonyloxy,
(C3-C8)-cycloalkenyl-(C1-C6)-alkoxycarbonyloxy and
(C3-C8)-cycloalkenyl-(C1-C6)-haloalkoxycarbonyloxy;
[0041] (C3-C8)-cycloalkylthio, (C3-C8)-alkenylthio,
(C3-C8)-cycloalkenylthio and (C3-C6)-alkynylthio;
[0042] hydroxy-(C1-C6)-alkyl, hydroxy-(C1-C6)-alkoxy,
cyano-(C1-C6)-alkoxy and cyano-(C1-C6)-alkyl; [0043]
3-oxetanyloxy-, [0044] C(O)NHR9 or --C(O)NR9R10, where
R9 and R10 are each independently of one another selected from
the group consisting of hydrogen, (C1-C6)-alkyl,
(C3-C6)-cycloalkyl, (C1-C6)-haloalkyl, or where
R9 and R10 together form a (C1-C6)-alkylene group
which may contain an oxygen or a sulfur atom or one or two amino or
(C1-C6)-alkylamino groups, [0045] where [0046] (1) the
radicals defined above for R3 to R7 may optionally be
cyclically attached to one another, with the proviso that they are ortho
to one another; and/or [0047] (2) two substituents which are ortho to one
another together form a (C1-C6)-alkylene group which may
contain one or more oxygen and/or sulfur atoms, where the
(C1-C6)-alkylene group may be mono- or polysubstituted by
halogen and the respective halogen substituents may be identical or
different; and/or [0048] (3) the radicals R1 and R2 mentioned
above may be mono- or polysubstituted and independently of one another
may be substituted by radicals selected from the group consisting of
halogen and (C1-C6)-alkyl; and [0049] (4) at least one radical
selected from the group of the radicals R3 to R7 is not
hydrogen, except for the compound
2-[(1,3-benzodioxol-5-ylmethyl)sulfanyl]-4-methyl-1,3-oxazole.

[0050] The compounds defined above comprise, at the aryl radical, at least
one radical R3 to R7 which is not hydrogen; i.e. the aryl
radical comprises, in addition to the radical --(CH2)--S(O)n--,
at least one further substituent which is not hydrogen, or such compounds
are not embraced by the definition according to the invention of the
compounds of the formula (I) in which the aryl ring is unsubstituted.

[0051] In addition, the definition according to the invention of the
compounds of the formula (I) does in particular not comprise compounds in
which R1 and/or R2 have the meaning (C6)-aryl at the
oxazole ring.

[0052] If the radicals R1 to R7, in particular cycloalkyl, are
substituted, the substituents are preferably selected from the group
consisting of (C1-C6)-alkyl, (C1-C6)-haloalkyl,
(C1-C6)-alkoxy, nitro, cyano, (C1-C3)-cycloalkyl,
(C1-C6)-haloalkoxy, (C1-C6)-alkylthio,
(C1-C6)-alkylcarbonyl, (C1-C6)-alkoxycarbonyl or
halogen, where these radicals of the second substituent level may
optionally be cyclically attached to one another, with the proviso that
they are ortho to one another.

[0053] The overlap with the disclosure of the medical publication JP 620
39 583 A has been taken into account by a disclaimer which excludes the
compound 2-[(1,3-benzodioxol-5-ylmethyl)sulfanyl]-4-methyl-1,3-oxazole
from the scope of the invention.

[0054] A first embodiment of the present invention comprises compounds of
the formula (I) in which [0055] R1 is preferably selected from the
group consisting of hydrogen, halogen, nitro, cyano, carboxyl,
(C1-C6)-alkyl, (C3-C6)-cycloalkyl,
(C3-C6)-cycloalkoxy, (C1-C6)-alkoxy,
(C1-C6)-alkylcarbonyl, (C3-C6)-cycloalkylcarbonyl,
(C1-C6)-alkoxycarbonyl, (C3-C6)-cycloalkoxycarbonyl,
mono-((C1-C4)-alkyl)amino-carbonyl,
di-((C1-C4)-alkyl)aminocarbonyl,
mono-((C1-C4)-alkyl)aminosulfonyl,
di-((C1-C4)-alkyl)aminosulfonyl, (C1-C4)-alkylthio,
(C3-C6)-cycloalkylthio, (C1-C4)-alkylsulfinyl,
(C3-C6)-cycloalkylsulfinyl, (C1-C4)-alkylsulfonyl,
(C3-C6)-cycloalkylsulfonyl, (C1-C4)-alkylsulfonyloxy,
(C3-C6)-cyclo-alkylsulfonyloxy, (C2-C3)-alkenyl,
(C2-C3)-alkynyl, (C2-C3)-alkenyloxy,
(C2-C3)-alkynyloxy, --NHCO--(C1-C3)-alkyl,
--NHCO2--(C1-C3)-alkyl, --NHCONH--(C1-C3)-alkyl,
--NHSO2--(C1-C3)-alkyl, --OCONH--(C1-C3)-alkyl,
--CONHR9, --CONR9R10, where R9 and R10 are
independently of one another selected from the group consisting of
hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl and
(C1-C6)-haloalkyl; and [0056] where the radical R1 may be
mono- or polysubstituted by radicals selected from the group consisting
of halogen and (C1-C6)-alkyl; R1 is particularly [0057]
preferably selected from the group consisting of H, F, CI, Br, I, Me, Et,
NO2, C(O)OEt, CHF2 and CF3; and R1 is very
particularly [0058] preferably selected from the group consisting of H,
F, CI, Br, I, Me, and NO2.

[0059] A second embodiment of the present invention comprises compounds of
the formula (I) in which [0060] R2 is preferably selected from the
group consisting of hydrogen, halogen, nitro, cyano, carboxyl,
(C1-C6)-alkyl, (C3-C6)-cycloalkyl,
(C3-C6)-cycloalkoxy, (C1-C6)-alkoxy,
(C1-C6)-alkylcarbonyl, (C3-C6)-cycloalkylcarbonyl,
(C1-C6)-alkoxycarbonyl, (C3-C6)-cycloalkoxycarbonyl,
mono-((C1-C4)-alkyl)amino-carbonyl,
di-((C1-C4)-alkyl)aminocarbonyl,
mono-((C1-C4)-alkyl)aminosulfonyl,
di-((C1-C4)-alkyl)aminosulfonyl, (C1-C4)-alkylthio,
(C3-C6)-cycloalkylthio, (C1-C4)-alkylsulfinyl,
(C3-C6)-cycloalkylsulfinyl, (C1-C4)-alkylsulfonyl,
(C3-C6)-cycloalkylsulfonyl, (C1-C4)-alkylsulfonyloxy,
(C3-C6)-cyclo-alkylsulfonyloxy, (C2-C3)-alkenyl,
(C2-C3)-alkynyl, (C2-C3)-alkenyloxy,
(C2-C3)-alkynyloxy, --NHCO--(C1-C3)-alkyl,
--NHCO2--(C1-C3)-alkyl, --NHCONH--(C1-C3)-alkyl,
--NHSO2--(C1-C3)-alkyl, --OCONH--(C1-C3)-alkyl,
--CONNR9, --CONR9R10, where R9 and R10 are
independently of one another selected from the group consisting of
hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl and
(C1-C6)-haloalkyl; and [0061] where the radical R2 may be
mono- or polysubstituted by radicals selected from the group consisting
of halogen and (C1-C6)-alkyl; R2 is particularly [0062]
preferably selected from the group consisting of H, F, CI, Br, I, Me, Et,
NO2, C(O)OEt, CHF2 and CF3; and R2 is very
particularly [0063] preferably selected from the group consisting of H,
F, CI, Br and I.

[0068] A fourth embodiment of the present invention comprises compounds of
the formula (I) in which [0069] R4 is preferably selected from the
group consisting of hydrogen, hydroxyl, halogen, cyano, nitro, amino,
C(O)OH, (C1-C4)-alkyl, (C3-C6)-cycloalkyl,
(C1-C4)-haloalkyl, (C1-C4)-alkoxy,
(C1-C4)-haloalkoxy,
(C1-C4)-alkoxy-(C1-C2)-alkyl,
(C1-C3)-alkylcarbonyl, (C1-C3)-alkylcarbonyloxy,
(C1-C4)-alkoxycarbonyl, (C3-C6)-cycloalkoxycarbonyl,
(C3-C6)-cycloalkyl-(C1-C2)-alkoxy,
(C3-C6)-cycloalkoxy,
(C1-C4)-alkoxycarbonyl-(C1-C2)-alkoxy,
(C3-C4)-alkenyloxy, (C3-C4)-alkynyloxy,
(C1-C4)-alkylthio, (C1-C4)-haloalkylthio,
(C1-C4)-alkylsulfinyl, (C1-C4)-haloalkylsulfinyl,
(C1-C4)-alkylsulfonyl, (C1-C4)-haloalkylsulfonyl,
(C1-C4)-alkylsulfonyloxy, di-(C1-C4)-alkylamino,
(C3-C4)-alkenyloxycarbonyl,
(C2-C4)-alkynyloxycarbonyl, formyl, (C2-C4)-alkenyl,
(C2-C4)-alkynyl, --C(O)NR9R10, where R9 and
R10 are independently of one another selected from the group
consisting of hydrogen, (C1-C6)-alkyl,
(C3-C6)-cycloalkyl, (C1-C6)-haloalkyl, or where
R9 and R10 together form a (C1-C6)-alkylene group
which may contain an oxygen or sulfur atom or one or two amino or
(C1-C6)-alkylamino groups; R4 is particularly [0070]
preferably selected from the group consisting of H, F, CI, Br, OH,
NO2, Me, iPr, CHF2, CF3, OMe, OEt, OPr, OiPr, OBu,
OCHF2, OCF3, OCH2CF3, C(O)OH and C(O)OMe; R4 is
very particularly [0071] preferably selected from the group consisting of
H, F, CI, Me, CF3 and OMe.

[0072] A fifth embodiment of the present invention comprises compounds of
the formula (I) in which [0073] R5 is preferably selected from the
group consisting of hydrogen, hydroxyl, halogen, cyano, nitro, amino,
C(O)OH, (C1-C4)-alkyl, (C3-C6)-cycloalkyl,
(C1-C4)-haloalkyl, (C1-C4)-alkoxy,
(C1-C4)-haloalkoxy,
(C1-C4)-alkoxy-(C1-C2)-alkyl,
(C1-C3)-alkylcarbonyl, (C1-C3)-alkylcarbonyloxy,
(C1-C4)-alkoxycarbonyl, (C3-C6)-cycloalkoxycarbonyl,
(C3-C6)-cycloalkyl-(C1-C2)-alkoxy,
(C3-C6)-cycloalkoxy,
(C1-C4)-alkoxycarbonyl-(C1-C2)-alkoxy,
(C3-C4)-alkenyloxy, (C3-C4)-alkynyloxy,
(C1-C4)-alkylthio, (C1-C4)-haloalkylthio,
(C1-C4)-alkylsulfinyl, (C1-C4)-haloalkylsulfinyl,
(C1-C4)-alkylsulfonyl, (C1-C4)-haloalkylsulfonyl,
(C1-C4)-alkylsulfonyloxy, di-(C1-C4)-alkylamino,
(C3-C4)-alkenyloxycarbonyl,
(C2-C4)-alkynyloxycarbonyl, formyl, (C2-C4)-alkenyl,
(C2-C4)-alkynyl, --C(O)NR9R10, where R9 and
R10 are independently of one another selected from the group
consisting of hydrogen, (C1-C6)-alkyl,
(C3-C6)-cycloalkyl, (C1-C6)-haloalkyl, or where
R9 and R10 together form a (C1-C6)-alkylene group
which may contain an oxygen or sulfur atom or one or two amino or
(C1-C6)-alkylamino groups; R5 is particularly [0074]
preferably selected from the group consisting of H, F, Cl, Br, OH, Me,
CF3, OMe, OCHF2, OCF3, OCH2CF3, C(O)OMe and
C(O)OEt; and R5 is very particularly [0075] preferably selected from
the group consisting of H, F, CI, Br, CF3 and Me.

[0076] A sixth embodiment of the present invention comprises compounds of
the formula (I) in which [0077] R6 is preferably selected from the
group consisting of hydrogen, hydroxyl, halogen, cyano, nitro, amino,
C(O)OH, (C1-C4)-alkyl, (C3-C6)-cycloalkyl,
(C1-C4)-haloalkyl, (C1-C4)-alkoxy,
(C1-C4)-haloalkoxy,
(C1-C4)-alkoxy-(C1-C2)-alkyl,
(C1-C3)-alkylcarbonyl, (C1-C3)-alkylcarbonyloxy,
(C1-C4)-alkoxycarbonyl, (C3-C6)-cycloalkoxycarbonyl,
(C3-C6)-cycloalkyl-(C1-C2)-alkoxy,
(C3-C6)-cycloalkoxy,
(C1-C4)-alkoxycarbonyl-(C1-C2)-alkoxy,
(C3-C4)-alkenyloxy, (C3-C4)-alkynyloxy,
(C1-C4)-alkylthio, (C1-C4)-haloalkylthio,
(C1-C4)-alkylsulfinyl, (C1-C4)-haloalkylsulfinyl,
(C1-C4)-alkylsulfonyl, (C1-C4)-haloalkylsulfonyl,
(C1-C4)-alkylsulfonyloxy, di-(C1-C4)-alkylamino,
(C3-C4)-alkenyloxycarbonyl,
(C2-C4)-alkynyloxycarbonyl, formyl, (C2-C4)-alkenyl,
(C2-C4)-alkynyl, --C(O)NR9R10, where R9 and
R10 are independently of one another selected from the group
consisting of hydrogen, (C1-C6)-alkyl,
(C3-C6)-cycloalkyl, (C1-C6)-haloalkyl, or where
R9 and R10 together form a (C1-C6)-alkylene group
which may contain an oxygen or sulfur atom or one or two amino or
(C1-C6)-alkylamino groups; R6 is particularly [0078]
preferably selected from the group consisting of H, F, CI, Br, NO2,
Me, iPr, OMe, OEt, OPr, OiPr, OBu, OCHF2, CF3, OCF3,
OCH2CF3, OCH2CH═CH2 and OCH2C≡CH; and
R6 is very particularly [0079] preferably selected from the group
consisting of H, F, Cl, Me, CF3 and OMe.

[0080] A seventh embodiment of the present invention comprises compounds
of the formula (I) in which [0081] R' is preferably selected from the
group consisting of hydrogen, hydroxyl, halogen, cyano, nitro, amino,
C(O)OH, (C1-C4)-alkyl, (C3-C6)-cycloalkyl,
(C1-C4)-haloalkyl, (C1-C4)-alkoxy,
(C1-C4)-haloalkoxy,
(C1-C4)-alkoxy-(C1-C2)-alkyl,
(C1-C3)-alkylcarbonyl, (C1-C3)-alkylcarbonyloxy,
(C1-C4)-alkoxycarbonyl, (C3-C6)-cycloalkoxycarbonyl,
(C3-C6)-cycloalkyl-(C1-C2)-alkoxy,
(C3-C6)-cycloalkoxy,
(C1-C4)-alkoxycarbonyl-(C1-C2)-alkoxy,
(C3-C4)-alkenyloxy, (C3-C4)-alkynyloxy,
(C1-C4)-alkylthio, (C1-C4)-haloalkylthio,
(C1-C4)-alkylsulfinyl, (C1-C4)-haloalkylsulfinyl,
(C1-C4)-alkylsulfonyl, (C1-C4)-haloalkylsulfonyl,
(C1-C4)-alkylsulfonyloxy, di-(C1-C4)-alkylamino,
(C3-C4)-alkenyloxycarbonyl,
(C2-C4)-alkynyloxycarbonyl, formyl, (C2-C4)-alkenyl,
(C2-C4)-alkynyl, --C(O)NR9R10, where R9 and
R10 are independently of one another selected from the group
consisting of hydrogen, (C1-C6)-alkyl,
(C3-C6)-cycloalkyl, (C1-C6)-haloalkyl, or where
R9 and R10 together form a (C1-C6)-alkylene group
which may contain an oxygen or sulfur atom or one or two amino or
(C1-C6)-alkylamino groups; R7 is particularly [0082]
preferably selected from the group consisting of H, F, CI, Br, OH,
NO2, NMe2, NEt2, Me, Et, CHF2, CF3, OMe, OEt,
OPr, OiPr, OBu, OiBu, OCHF2, OCF3, OCH2CF3, C(O)OH,
C(O)OMe, C(O)OEt, C(O)OPr, C(O)OiPr, C(O)OBu, C(O)OiBu, C(O)OsBu,
C(O)OCH2Ph, OCH2CH═CH2 and OCH2CECH; and R7
is very particularly [0083] preferably selected from the group consisting
of H, F, CI, Me, CF3, OCHF2, OCF3 and OMe.

[0084] Primarily for reasons of higher herbicidal activity, better
selectivity and/or better producibility, compounds of the formula (I)
according to the invention or their salts are of particular interest in
which individual radicals have one of the preferred meanings already
specified or specified below, or in particular those in which one or more
of the preferred meanings already specified or specified below occur in
combination.

[0085] The abovementioned general or preferred radical definitions apply
both to the end products of the formula (I) and, correspondingly, to the
starting materials or the intermediates required in each case for the
preparation. These radical definitions can be exchanged for one another
as desired, i.e. including combinations between the given preferred
ranges.

[0086] For the possible combinations of the various substituents of the
formula (I) the general principles of the construction of chemical
compounds have to be observed, i.e. the formula (I) does not comprise any
compounds known to the person skilled in the art as being chemically
impossible.

[0087] In the context of these first to seventh embodiments of the present
invention, it is possible to combine the individual preferred,
particularly preferred and very particularly preferred meanings of the
substituents R1 to R7 with one another as desired. This means
that the present invention embraces compounds of the formula (I) in
which, for example, the substituent R1 has a preferred meaning and
the substituents R4 to R7 have the general meaning or else, for
example, the substituent R1 has a preferred meaning, the substituent
R2 has a particularly preferred meaning, the substituent R3 has
a very particularly preferred meaning and the substituents R4 and
R7 have the general meaning.

[0088] The preferred, particularly preferred and very particularly
preferred definitions of the radicals R3 to R7 at the aryl ring
given in these embodiments of the present invention can be combined in
any combination with the meanings defined in the present invention as
preferred, particularly preferred and very particularly preferred of the
substituents R1 and R2 at the oxazole ring.

[0089] In the context of the present invention, the compounds of the
formula (I) also comprise compounds quaternized at a nitrogen atom by a)
protonation, b) alkylation or c) oxidation.

[0090] If appropriate, the compounds of the formula (I) are able to form
salts by forming an adduct with a suitable inorganic or organic acid,
such as, for example, HCl, HBr, H2SO4 or HNO3, or else
oxalic acid or sulfonic acids, to a basic group, such as, for example,
amino or alkylamino. Suitable substituents present in deprotonated form,
such as, for example, sulfonic acids or carboxylic acids, are capable of
forming inner salts with groups, such as amino groups, which can be
protonated for their part. Salts can also be formed by replacing the
hydrogen of suitable substituents, such as, for example, sulfonic acids
or carboxylic acids, with a cation suitable in the agrochemical sector.
These salts are, for example, metal salts, in particular alkali metal
salts or alkaline earth metal salts, especially sodium salts and
potassium salts, or else ammonium salts, salts with organic amines or
quaternary ammonium salts having cations of the formula
[NRR'R''R'''].sup.+ in which R to R''' in each case independently are an
organic radical, in particular alkyl, aryl, arylalkyl or alkylaryl.

[0091] In the formula (I) and in all the other formulae of the present
invention, the radicals alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino,
alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylsulfinyl
and haloalkylsulfonyl and the corresponding unsaturated and/or
substituted radicals can in each case be straight-chain or branched in
the carbon skeleton. Unless indicated specifically, preference is given
for these radicals to the lower carbon skeletons, for example those
having 1 to 6 carbon atoms, especially 1 to 4 carbon atoms, or in the
case of unsaturated groups having 2 to 6 carbon atoms, especially 2 to 4
carbon atoms. Alkyl radicals, also in composite definitions such as
alkoxy, haloalkyl, etc., are for example methyl; ethyl; n-propyl or
isopropyl; n-, iso-, t- or 2-butyl; pentyls, such as n-pentyl; hexyls,
such as n-hexyl, isohexyl and 1,3-dimethylbutyl; heptyls, such as
n-heptyl, 1-methylhexyl or 1,4-dimethylpentyl; alkenyl and alkynyl
radicals have the meaning of the possible unsaturated radicals
corresponding to the alkyl radicals; where at least one double bond or
triple bond is present in the radical, preferably one double bond or
triple bond, respectively. Alkenyl is, for example, vinyl, allyl,
1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl,
but-3-en-1-yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl; alkynyl
is, for example, ethynyl, propargyl, but-2-yn-1-yl, but-3-yn-1-yl and
1-methylbut-3-yn-1-yl.

[0093] The definition "substituted by one or more radicals" refers, unless
otherwise defined, to one or more identical or different radicals.

[0094] The substituents given by way of example ("first substituent
level") can, if this has not already been defined expressis verbis and if
they include hydrocarbon-containing fractions, be further substituted
therein if desired ("second substituent level"), for example by one of
the substituents as defined for the first substituent level.

[0095] Corresponding further substituent levels are possible. The term
"substituted radical" preferably embraces just one or two substituent
levels.

[0096] In the case of radicals having carbon atoms, preference is given to
those having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, in
particular 1 or 2 carbon atoms. Preference is generally given to
substituents from the group consisting of halogen, for example fluorine
and chlorine, (C1-C4)-alkyl, preferably methyl or ethyl,
(C1-C4)-haloalkyl, preferably trifluoromethyl,
(C1-C4)-alkoxy, preferably methoxy or ethoxy,
(C1-C4)-haloalkoxy, nitro and cyano.

[0097] The invention also provides all stereoisomers embraced by formula
(I), and mixtures thereof. Such compounds of the formula (I) contain one
or more asymmetric carbon atoms (=asymmetrically substituted carbon
atoms) and/or asymmetric sulfur atoms in the form of sulfoxides (i.e. in
the case of the compounds of the formula (I) where n=1), which can exist
in two enantiomeric forms, or else double bonds, which are not expressly
shown in the formula (I). Formula (I) embraces all possible
stereoisomers, such as enantiomers, diastereomers and Z and E isomers,
defined by their specific spatial form, and these stereoisomers can be
obtained by customary methods from mixtures of the stereoisomers or else
be prepared by stereoselective reactions in combination with the use of
stereochemically pure starting materials.

[0098] The present invention also provides methods for preparing the
compounds of the formula (I) and/or salts thereof. Compounds of the
formula (I) according to the invention can be prepared alternatively by
various analogous known methods described below in a nonlimiting way:

a.)

[0099] To prepare optically active sulfoxides of the formula (III) or
sulfones of the formula (IV) in which R1, R2, R3, R4,
R5, R6, R7 have the meanings given above for formula (I),

##STR00002##

for example, a thioether of the formula (II)

##STR00003##

in which R1, R2, R3, R4, R5, R6, R7
have the meanings given above for formula (I) is oxidized with one
equivalent of an oxidizing agent to give the optically active sulfoxides
(III) in which n is the number 1, or oxidized with two equivalents of an
oxidizing agent to give the sulfones (IV) in which n is the number 2. The
sulfones (IV) can also be obtained from the optically active sulfoxides
(III), where the oxidation is carried out using one equivalent of an
oxidizing agent, giving the sulfones (IV).

[0100] The oxidizing agents which can be used for this reaction are not
subject to any particular restrictions, it being possible to use
oxidizing agents which are capable of oxidizing corresponding sulfur
compounds to sulfoxide compounds.

[0101] Suitable oxidizing agents for preparing the optically active
sulfoxides (n=1) are inorganic peroxides such as, for example, hydrogen
peroxide, sodium metaperiodate, optionally in the presence of a catalyst
such as, for example, ruthenium(III) chloride, organic peroxides such as,
for example, tert-butyl hydroperoxide or organic peracids such as
peracetic acid or, preferably, 3-chloro-perbenzoic acid. The reaction can
be carried out in halogenated hydrocarbons, for example dichloromethane,
1,2-dichloroethane, an alcohol, such as, for example, methanol, or in
dimethylformamide, acetonitrile, water or acetic acid, or in a mixture of
the solvents mentioned above. The reaction is carried out in a
temperature range of between -80° C. and 120° C.,
preferably between -20° C. and 50° C. Such processes are
known in the literature and described, for example, in J. Org. Chem., 58
(1993) 2791, J. Org. Chem., 68 (2003) 3849 and J. Heterocyclic Chem., 15
(1978)

[0103] The enantioselective synthesis of chiral sulfoxides of the formula
(III) in optically enriched or pure form can be carried out from thio
compounds of the formula (II) using methods as described, for example, in
Chem. Rev., 103 (2003) 3651-3705 and in the literature cited therein, and
Adv. Synth. Catal., 347 (2005) 19-31 and in the literature cited therein.
In each individual case, the absolute configuration of the product
depends on the structure of the optically active catalyst.

##STR00004##

[0104] Compounds of the formula (III) consist of a mixture of the
respective enantiomers (III-S) and (III-R), which are chiral at the
sulfoxide function,

##STR00005##

where the radicals R1, R2, R3, R4, R5, R6,
R7 have the meaning given above for formula (I).

[0105] Thus, they have a chiral sulfur atom which, in the structure shown
above, is illustrated by the marker (R/S). According to the rules of
Cahn, Ingold and Prelog (CIP rules), this sulfur atom can have either an
(R) configuration or an (S) configuration.

[0106] The present invention encompasses compounds of the formula (III)
both with (S) and with (R) configuration, i.e. the present invention
encompasses the compounds of the formula (III) in which the sulfur atom
in question has [0107] (1) an (R) configuration; or [0108] (2) an (S)
configuration.

[0109] In addition, the scope of the present invention also encompasses
[0110] (3) any mixtures of compounds of the formula (III) having an (R)
configuration (compounds of the formula (III-(R)) with compounds of the
formula (III) having an (S) configuration (compounds of the formula
(III-(S)).

[0111] The present invention embraces racemic compounds of the formula
(III), i.e. where the compounds of the formula (III) having the (S)
configuration (compounds of the formula (III-S)) are, compared to the (R)
configuration (compounds of the formula (III-R)), present as a 1:1
mixture (stereochemical purity 50%).

[0112] However, within the context of the present invention, preference is
also given to compounds of the formula (III) having (S) configuration
(compounds of the formula (III-S)) as compared to the (R) configuration
(compounds of the formula (III-R)) having a stereochemical purity of in
general from more than 50% to 100%, preferably from 60 to 100%, in
particular from 80 to 100%, very particularly from 90 to 100%, especially
from 90 to 100%, very particularly preferably 95 to 100%, where the
particular (S) compound is preferably present with an enantioselectivity
of in each case more than 50% ee, preferably 60 to 100% ee, in particular
80 to 100% ee, very particularly 90 to 100% ee, most preferably 95 to
100% ee, based on the total content of (S) compound in question.

[0113] In the context of the present invention, preference is furthermore
also given to compounds of the formula (III) having the (R) configuration
(compounds of the formula (III-R)) as compared to the (S) configuration
(compounds of the formula (III-R)) having a stereochemical purity of in
general from more than 50% to 100%, preferably from 60 to 100%, in
particular from 80 to 100%, very particularly from 90 to 100%, especially
from 95 to 100%, where the respective (R) compound is preferably present
in an enantioselectivity of in each case more than 50% ee, preferably
from 60 to 100% ee, in particular from 80 to 100% ee, very particularly
from 90 to 100% ee, most preferably from 95 to 100% ee, based on the
total content of the respective (S) compound.

[0114] Accordingly, the present invention also relates to compounds of the
formula (III) in which the stereochemical configuration at the sulfur
atom (S) marked by (*) is of a stereochemical purity of from 60 to 100%
(S), preferably from 80 to 100% (S), in particular from 90 to 100% (S),
very particularly from 95 to 100% (S).

[0115] Suitable for preparing enantiomers of the formula (III) are, in
addition to enantioselective syntheses, also customary methods for the
separation of racemates (cf. textbooks of stereochemistry).

[0116] Racemic mixtures, for example of optically active sulfoxides of the
formula (III), can be separated by known processes. Such methods for the
separation of racemates are described in textbooks of stereochemistry,
for example in "Basic Organic Stereochemistry" (Eds.: Eliel, Ernest L.;
Wilen, Samuel H.; Doyle, Michael P.; 2001; John Wiley & Sons) and
"Stereochemistry of Organic Compounds" (Eds.: Eliel, Ernest L.; Wilen,
Samuel H.; Mander, Lewis N.; 1994; John Wiley & Sons). Suitable for this
purpose are, for example, adduct formation with an optically active
auxiliary, separation of the diastereomeric adducts into the
corresponding diastereomers, for example by crystallization,
chromatographic methods, especially column chromatography and high
pressure liquid chromatography, distillation, if appropriate under
reduced pressure, extraction and other methods and subsequent cleavage of
the diastereomers to afford the enantiomers. Suitable for preparative
amounts or on an industrial scale are processes such as the
crystallization of diastereomeric salts which can be obtained from the
compounds (III) using optically active acids and, if appropriate,
provided that acidic groups are present, using optically active bases.

[0118] The crystallizations are then in most cases carried out in aqueous
or aqueous-organic solvents, where the diastereomer which is less soluble
precipitates first, if appropriate after seeding. One enantiomer of the
compound of the formula (III) is then liberated from the precipitated
salt, or the other is liberated from the crystals, by acidification or
using a base.

[0119] Furthermore, racemates can be separated chromatographically using
chiral stationary phases. Such enantiomer separations can be carried out
in the mg to 100 kg range using preparative HPLC units operated
batch-wise or continuously.

[0120] The preparation of the thioethers of the formula (II) which serve
as starting material for the reaction described above under a.) and are
also part of the subject matter of the present invention is described
below under processes b.), c.), d.), e.), f.), g.) and h.).

b.)

[0121] To prepare a thioether of the formula (II),

##STR00006##

in which R1, R2, R3, R4, R5, R6, R7
have the meanings given above for formula (I), for example, a
2-mercaptooxazole or a salt thereof, preferably an alkali metal or
alkaline earth metal salt of the formula (V),

##STR00007##

in which R1, R2 have the meanings given above for formula (I),
is reacted with a benzyl derivative of the formula (VI)

##STR00008##

in which R3, R4, R5, R6, R7 have the meanings
given above for formula (I) and Lg is a leaving group, in the presence of
a suitable alkali metal or alkaline earth metal base, for example
potassium carbonate or sodium hydride, or an organic base such as, for
example, preferably 1,8-diazabicyclo(5.4.0)undec-7-ene (DBU), in a
suitable solvent, for example dimethylformamide, tetrahydrofuran,
ethanol, or preferably acetonitrile, in a temperature range between
0° C. and 100° C., and optionally under an atmosphere of an
inert gas, for example nitrogen.

[0123] Instead of the mercapto compounds mentioned or salts thereof,
preferably alkali metal or alkaline earth metal salts of the formula (V),
it is also possible to use mercaptan formers, such as, for example,
isothiuronium salts.

[0125] The 2-mercaptooxazole derivatives or the corresponding salts of the
2-mercaptooxazole derivatives of the formula (V) employed in process b.)
are known to the person skilled in the art, and some of them are
commercially available or can be prepared by processes known to the
person skilled in the art, for example as described in a) Science of
Synthesis, Houben-Weyl (Methods of Molecular Transformations), Category
2, Volume 11, Ed. E. Schaumann; b) Houben-Weyl (Methoden der organische
Chemie [Methods of Organic Chemistry]), Volume E8a, Hetarene III--part 1,
Ed. E. Schaumann; c) Can. J. Chem., Vol. 50, 3082-3083 (1972); d) WO
03/006442 A.

[0126] The benzyl derivatives of the formula (VI) employed in process b.)
are known to the person skilled in the art or available commercially or
can be prepared by processes known to the person skilled in the art [see,
for example: a) WO 01/12613 A, b) WO 02/062770 A, c) WO 03/000686 A, d)
WO 2006/024820 A].

c.)

[0127] Alternatively, the preparation of a thioether of the formula (II),

##STR00009##

in which R1, R2, R3, R4, R5, R6, R7
have the meanings given above for formula (I), can take place by reacting
an oxazole derivative of the formula (VII),

##STR00010##

in which R1, R2 have the meanings given above for formula (I)
and Lg' is a leaving group, suitable leaving groups being inter alia
fluorine, chlorine, bromine, iodine, sulfide, sulfoxide or sulfonate
groups, with a benzyl imidothiocarbamate salt of the formula (VIII)

##STR00011##

in which R3, R4, R5, R6, R7 have the meanings
given above for formula (I), Lg is a leaving group, in a one-pot process
in the presence of an aqueous alkali metal or alkaline earth metal base.

[0128] The reaction is represented in a general manner by the equation
below:

##STR00012##

[0129] The oxazole derivatives of the formula (VII) employed in process
c.) are known to the person skilled in the art or available commercially
or can be prepared by processes known to the person skilled in the art
[as described, for example, in "Science of Synthesis", Houben-Weyl
(Methods of Molecular Transformations), Category 2, Volume 11, Ed. E.
Schaumann and DE 26 25 229 A].

[0130] The use of imidothiocarbamate salts (isothiuronium salts) in the
sense of a one-pot reaction for hydrolyzing the imidothiocarbamate salt
(isothiuronium salt) and the reaction of the mercaptan intermediate in an
exchange reaction are described, for example, in DE 39 42 946 A, WO
2006/024820 A and WO 2006/037945 A, and under phase-transfer catalysis in
WO 2007/003294 A and WO 2007/003295 A.

[0131] Compounds of the formula (VIII) can be obtained by reacting an
alkylating agent of the formula (VI) in which R3, R4, R5,
R6, R7 have the meanings given above for formula (I) and Lg is
a leaving group with thiourea.

[0132] The preparation of the imidothiocarbamate salts (VIII) by reaction
of a benzylating agent of the formula (VI) with thiourea is carried out
by known processes (such as, for example, by the process described in DD
152557 A), preferably by reaction with an equimolar amount of thiourea
and optionally in the presence of an alkali metal iodide, for example
sodium iodide, potassium iodide, in an inert solvent such as a lower
alcohol, for example methanol, ethanol or isopropanol; a hydrocarbon, for
example benzene or toluene; a halogenated hydrocarbon, for example
dichloromethane or chloroform; or an ether derivative, for example methyl
tert-butyl ether, tetrahydrofuran or dioxane, at temperatures between 0
and 150° C., preferably between 20 and 100° C.

[0133] In the process according to the invention, the compounds of the
imidothiocarbamate salts of the formula (VIII), which in many cases are
obtained by crystallization, are generally reacted without any further
purification steps under vigorous stirring with equimolar amounts of the
oxazole derivatives of the formula (VII) under phase-transfer conditions.

[0134] Here, the reaction is advantageously carried out in a two-phase
system where, in addition to an aqueous strongly basic alkali metal or
alkaline earth metal hydroxide solution, preferably sodium hydroxide or
potassium hydroxide, with at least two equivalents of the base, the
organic phase is an inert solvent such as tetrahydrofuran, diethyl ether,
acetonitrile, pentane, hexane, benzene, toluene, xylene, chlorobenzene,
dichloromethane, chloroform, carbon tetrachloride, nitrobenzene or
mixtures of these solvents.

[0135] It is also possible to use a slightly subequimolar amount of the
respectively more valuable starting material of the formula (VIII) or of
the formula (VII).

[0137] The reactants and the catalyst are preferably stirred vigorously at
temperatures of from 20 to 100° C. under an atmosphere of
protective gas.

[0138] The mercaptan intermediate, formed under the reaction conditions,
of the formula (IX) in which R3, R4, R5, R6, R7
have the meaning given above for formula (I)

##STR00013##

immediately reacts in situ with the oxazole derivative of the formula
(VII). d.)

[0139] Alternatively, thioethers of the formula (II) in which R1,
R2, R3, R4, R5, R6, R7 have the meanings
given above for formula (I)

##STR00014##

can be prepared by reacting an oxazole derivative of the formula (VII)

##STR00015##

in which R1, R2 have the meanings given above for formula (I)
and Lg' is a leaving group, suitable leaving groups being chlorine,
bromine or methylsulfonyl groups, inter alia, with a benzyl
imidothiocarbamate salt (isothiuronium salt) of the formula (VIII)

##STR00016##

in which R3, R4, R5, R6, R7 have the meanings
given above for formula (I), Lg is a leaving group, in a one-pot process
in the presence of an alkali metal or alkaline earth metal carbonate base
and a solvent such as an alcohol.

[0140] The reaction is represented in a general manner by the equation
below:

##STR00017##

[0141] Compounds of the formula (VIII) can be obtained by reacting an
alkylating agent of the formula (VI) in which R3, R4, R5,
R6, R7 have the meanings given above for formula (I) and Lg is
a leaving group with thiourea, as described in process c.) above.

[0142] In the process according to the invention, the imidothiocarbamate
salts (isothiuronium salts) of the formula (VIII) are generally reacted
without any further purification steps under vigorous stirring with a
slight excess of the oxazole derivatives of the formula (VII) and with a
slight excess of a carbonate base, for example potassium carbonate,
sodium carbonate or potassium bicarbonate, or a hydroxide, for example
potassium hydroxide, or an alkoxide, for example a sodium alkoxide, in an
alcohol, for example ethanol, an ether, for example 1,4-dioxane,
tetrahydrofuran; a polar solvent such as, for example, water,
dimethylformamide; or a mixture of these solvents in a temperature range
between 20 and 200° C., preferably between 50 and 150° C.,
optionally under an atmosphere of an inert gas, for example nitrogen, or
in a microwave apparatus.

[0143] The imidothiocarbamate salts (isothiuronium salts) of the formula
(VIII) can also be reacted further in situ, without isolation.

[0144] Here, the reaction is advantageously carried out in an alcohol,
preferably ethanol, using at least 1.1 equivalents of the base,
preferably potassium carbonate (K2CO3).

[0145] Such processes are known in the literature and described, for
example, in WO 2006/024820 A, WO 01/012613 A and WO 2006/123088 A.

[0146] The oxazole derivatives of the formula (VII) employed in process
d.) are known to the person skilled in the art or available commercially,
or they can be prepared by processes known to the person skilled in the
art [see, for example, Science of Synthesis, Houben-Weyl (Methods of
Molecular Transformations), Category 2, Volume 11, Ed. E. Schaumann].

e.)

[0147] Alternatively, a thioether of the formula (II),

##STR00018##

in which R1, R2, R3, R4, R5, R6, R7
have the meanings given above for formula (I), can be prepared by
reacting an oxazole derivative of the formula (VII),

##STR00019##

in which R1, R2 have the meanings given above for formula (I)
and Lg' is a leaving group, suitable leaving groups being fluorine,
chlorine, bromine or sulfonate groups, inter alia, with a benzyl
mercaptan of the formula (IX),

##STR00020##

in which R3, R4, R5, R6, R7 have the meaning
given above for formula (I), in the presence of an alkali metal or
alkaline earth metal base, for example potassium carbonate or sodium
hydride, or an organic base, for example preferably
1,8-diazabicyclo(5.4.0)undec-7-ene (DBU), optionally in a solvent, for
example dimethylformamide, tetrahydrofuran, ethanol, or preferably
acetonitrile, in a temperature range between 0 and 100° C., and
optionally under an atmosphere of an inert gas, for example nitrogen.

[0148] Some of the processes are known from the literature and are
described, for example, in WO 2006/024820 A, WO 01/012613 A and WO
2006/123088 A.

[0149] Nucleophilic substitutions at oxazole derivatives have been
described in the literature, such as, for example, in Yamanaka, H.; Ohba,
S.; Sakamoto, T.; Heterocycles (1990), 31(6), 1115-27.

[0150] The oxazole derivatives of the formula (VII) employed in process
e.) are known to the person skilled in the art or available commercially
or can be prepared by processes known to the person skilled in the art
[see, for example, Science of Synthesis, Houben-Weyl (Methods of
Molecular Transformations), Category 2, Volume 11, Ed. E. Schaumann].

[0151] The mercaptans of the formula (IX) employed in process e.) are
known to the person skilled in the art (see, for example, WO 2004/013106
A) or can be prepared analogously to processes, known to the person
skilled in the art, for preparing mercaptans.

f.)

[0152] Thioethers of the formula (II) in which R1, R2, R3,
R4, R4, R5, R6, R7 have the meanings given above
for formula (I) and R1 represents halogen or nitro

##STR00021##

can be prepared, for example, by reacting an oxazole derivative of the
formula (X),

##STR00022##

in which R2, R3, R4, R5, R6, R7 have the
meanings given above for formula (I). The reaction is represented in a
general manner by the equation below:

##STR00023##

[0153] The compounds of the formula (X) are treated with a halogenating
agent such as, for example, halogen, such as chlorine, bromine, iodine or
a halosuccinimide, such as N-chlorosuccinimide (NCS), N-bromosuccinimide
(NBS), N-iodosuccinimide (NIS), or for nitro with a nitrating agent such
as, for example, nitrating acid prepared from sulfuric acid and nitric
acid, and reacted in suitable solvents such as chlorinated hydrocarbons,
for example carbon tetrachloride, dichloromethane, 1,2-dichloroethane or
dimethylformamide to give compounds of the formula (II).

[0154] The analogous thioether derivatives of the formula (X) employed in
process f.) can be prepared by processes known to the person skilled in
the art (see, for example: DE 26 25 229 A, WO 99/52874 A, WO 01/66529 A,
WO 95/24403 A; or by the processes mentioned above under b.), c.), d.),
e.).

g.)

[0155] Thioethers of the formula (II) in which R1, R2, R3,
R4, R5, R6, R7 have the meanings given above for
formula (I)

##STR00024##

can be prepared, for example, by reacting an oxazole derivative of the
formula (XI),

##STR00025##

prepared from an oxazole derivative of the formula (V) by reaction with
an alkylating agent R12Lg'' in which R2 has the meanings given
above for formula (I), R12 is preferably (C1-C6)-alkyl
which is unsubstituted or substituted by one or more identical or
different radicals from the halogen group, particularly preferably methyl
or ethyl, and Lg' is a leaving group, suitable leaving groups being
chlorine, bromine or methylsulfonyl groups, inter alia, with a strong
base and an alkylating agent R1Lg', in which R1 has the
meanings given above for formula (I), according to the equation

##STR00026##

in which R1, R2, R3, R4, R5, R6, R7
have the meanings given above for formula (I) and Lg or Lg' is a leaving
group, suitable leaving groups being, inter alia, fluorine, chlorine,
bromine, iodine or sulfonate groups such as methane-, trifluoromethane-,
ethane-, phenyl- or toluenesulfonate.

[0156] The strong base used can be lithium diisopropylamide (LDA), lithium
tetramethylpiperidine (LTMP), lithium hexamethyldisilazane (LHMDS),
preferably LDA, which can be prepared by processes known to the person
skilled in the art.

[0157] Hexamethylphosphoric triamide (HMPT), for example, can be used as
cosolvent. Inert solvents such as hydrocarbons such as, for example,
hexane, heptane, cyclohexane, aromatic hydrocarbons such as, for example,
benzene, ethers such as, for example, diethyl ether, methyl tert-butyl
ether (MTBE), tetrahydrofuran and dioxane, preferably tetrahydrofuran,
serve as solvents. The solvents mentioned above can also be used as
mixtures.

[0158] In this reaction, the compounds of the formula (XI) and the base or
the alkylating agent R1Lg' are preferably employed in amount of
0.9-1.5 mol of the latter per mole of the former. The reaction is
preferably carried out in a temperature range between -90° C. and
the boiling point of the solvent. The reaction time is not subject to any
restriction; in general, the reactions will have gone to completion after
1 to 24 hours.

[0159] For preparing the sulfones and sulfoxides of the compounds of the
formula (II) in which R1, R2, R3, R4, R5,
R6, R7 have the meanings given above for formula (I), it is
possible to use the method given under a).

[0160] In particular in the case that R1 is fluorine, preference is
given to using reagents for electrophilic fluorination, such as, for
example, 1-chloromethyl-4-fluoro-1,4-diazabicyclo[2,2,2]octane
bistetrafluoroborate (F-TEDA-BF4, SelectFluor®),
N-fluorobenzenesulfonimide (NFBS or NFSi),
N-fluoro-o-benzenedisulfonimide (NFOBS),
1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane
bis(tetrafluoroborate) (NFTh, AccuFluor®) and others, as described in
"Modern Fluoroorganic Chemistry", 2004, Wiley-VCH Verlag, Ed. P. Kirsch.

[0161] The 2-mercaptooxazole derivatives or the corresponding salts of the
2-mercaptooxazole derivatives of the formula (V) employed in process g.)
are known to the person skilled in the art or available commercially or
can be prepared by processes known to the person skilled in the art, for
example as described in Science of Synthesis, Houben-Weyl (Methods of
Molecular Transformations), Category 2, Volume 11, Ed. E. Schaumann.

[0162] Analogously to processes known to the person skilled in the art, it
is possible to deprotonate oxazole derivatives (X1) regioselectively in
the 5-position. Analogous reactions using an alkyl base such as
buthyllithium have been described in the literature, for example in
Boger, D. L. et al; J. Med. Chem. (2007) 50 (33), 1058-1068 and Molinski,
T. F. et al; J. Org. Chem. (1998) 63, 551-555, and using tea-butyllithium
and a copper salt in Marino, J. P.; Nguyen, N. Tet. Lett. (2003) 44,
7395-7398 and the literature cited therein.

[0163] The oxazole derivatives of the formula (XI) employed in process g.)
can be prepared, for example, according to process b.) by reacting a
2-mercaptooxazole derivative of the formula (V) with an alkylating agent
R12Lg' or according to processes known to the person skilled in the
art [see, for example, Science of Synthesis, Houben-Weyl (Methods of
Molecular Transformations), Category 2, Volume 11, Ed. E. Schaumann], or
they are commercially available.

[0164] The compounds of the formula (XIII) mentioned in process g.) can be
prepared from the compounds of the formula (XII) by oxidation according
to process a) above or by processes known to the person skilled in the
art. In turn, the compounds of the formula (XIII) can be reacted by the
above process c.) or d.) with benzyl imidothiocarbamate salts (VIII) or
with benzyl mercaptans of the formula (IX) according to the above process
e.) to give compounds of type (II).

h.)

[0165] Thioethers of the formula (II) in which R1, R2, R3,
R4, R5 have the meanings given above for formula (I)

##STR00027##

can also be prepared, for example, by reacting a benzyl disulfide
derivative of the formula (XV) with 2-aminooxazoles of the formula (XIV)
and a diazotizing agent, as shown in the equation below

##STR00028##

in which R1, R2, R3, R4, R5 have the meanings
given above for formula (I).

[0166] The benzyl disulfides of the formula (XV) are reacted with a
diazotizing agent and a 2-aminooxazole derivative of the formula (XIV) in
a suitable solvent to give compounds of the formula (II).

[0168] The diazotizing agent may, for example, be a nitrite ester, such as
isoamyl nitrite, or a nitrite salt, such as sodium nitrite. The molar
ratios can be chosen as desired; equimolar amounts of heteroarylalkyl
disulfides and diazotizing agents are preferred. The reaction is
preferably carried out at a temperature between -20° C. and the
boiling point of the chosen solvent and is generally gone to completion
after a period of from 0.1 to 40 hours.

[0170] The oxazole derivatives of the formula (XIV) employed in process
h.) are known to the person skilled in the art or available commercially,
or they can be prepared by processes known to the person skilled in the
art [see, for example, Science of Synthesis, Houben-Weyl (Methods of
Molecular Transformations], Category 2, Volume 11, Ed. E. Schaumann.

[0171] The benzyl disulfides of the formula (XV) can be prepared by
processes known to the person skilled in the art, for example as in
Gladysz, J. A., Wong, V. K., Jick, B. S.; Tetrahedron (1979) 35, 2329.

[0172] Preferred leaving groups Lg are halogens, for example chlorine,
bromine, iodine, or alkyl- or arylsulfonyl groups, such as methyl-,
ethyl-, phenyl- or tolylsulfonyl, or a haloalkylsulfonyl group, such as
trifluoromethyl, or nitro; however, particular preference is given to
chlorine and methylsulfonyl.

[0173] Preferred leaving groups Lg' are halogens, for example chlorine,
bromine, iodine, or alkyl- or arylsulfonyl groups, such as methyl-,
ethyl-, phenyl- or tolylsulfonyl, or a haloalkylsulfonyl group, such as
trifluoromethyl, or nitro; however, particular preference is given to
chlorine and methylsulfonyl.

[0174] A preferred group R12 is (C1-C6)-alkyl which is
unsubstituted or optionally substituted by one or more identical or
different radicals from the halogen group, particularly preferably methyl
or ethyl.

[0175] The present compounds of the formula (I) where n=1 (compounds of
the formula (III)) have a chiral sulfur atom which, in the structure
shown above, is illustrated by the marker (*). According to the rules of
Cahn, Ingold and Prelog (CIP rules), this sulfur atom can have either an
(R) configuration or an (S) configuration.

[0176] Thus, they have a chiral sulfur atom which, in the structure shown
above, is illustrated by the marker (R/S). According to the rules of
Cahn, Ingold and Prelog (CIP rules), this sulfur atom can have either an
(R) configuration or an (S) configuration.

[0177] The present invention encompasses--as already mentioned--compounds
of the formula (III) both with (S) and with (R) configuration, i.e. the
present invention encompasses the compounds of the formula (I) in which
the sulfur atom in question has [0178] (1) an (R) configuration; or
[0179] (2) an (S) configuration.

[0180] In addition, the scope of the present invention also encompasses
[0181] (3) any mixtures of compounds of the formula (III) having an (R)
configuration (compounds of the formula (III-(R)) with compounds of the
formula (III) having an (S) configuration (compounds of the formula
(III-(S)).

[0182] The present invention embraces racemic compounds of the formula
(III), i.e. where the compounds of the formula (III) having the (S)
configuration (compounds of the formula (III-S)) are, compared to the (R)
configuration (compounds of the formula (III-R)), present as a 1:1
mixture (stereochemical purity 50%).

[0183] However, within the context of the present invention, preference is
also given to compounds of the formula (III) having (S) configuration
(compounds of the formula (III-S)) as compared to the (R) configuration
(compounds of the formula (III-R)) having a stereochemical purity of in
general from more than 50% to 100%, preferably from 60 to 100%, in
particular from 80 to 100%, very particularly from 90 to 100%, especially
from 95 to 100%, where the particular (S) compound is preferably present
with an enantioselectivity of in each case more than 50% ee, preferably
60 to 100% ee, in particular 80 to 100% ee, very particularly 90 to 100%
ee, most preferably 95 to 100% ee, based on the total content of (S)
compound in question.

[0184] In the context of the present invention, preference is furthermore
also given to compounds of the formula (III) having the (R) configuration
(compounds of the formula (III-R)) as compared to the (S) configuration
(compounds of the formula (III-R)) having a stereochemical purity of in
general from more than 50% to 100%, preferably from 60 to 100%, in
particular from 80 to 100%, very particularly from 90 to 100%, especially
from 95 to 100%, where the respective (R) compound is preferably present
in an enantioselectivity of in each case more than 50% ee, preferably
from 60 to 100% ee, in particular from 80 to 100% ee, very particularly
from 90 to 100% ee, most preferably from 95 to 100% ee, based on the
total content of the respective (S) compound.

[0185] Accordingly, the present invention also relates to compounds of the
formula (III) in which the stereochemical configuration at the sulfur
atom (S) marked by (*) is of a stereochemical purity of from 60 to 100%
(S), preferably from 80 to 100% (S), in particular from 90 to 100% (S),
very particularly from 95 to 100% (S).

[0186] Depending on the type and attachment of the substituents, the
compounds of the formula (III) may contain further centers of chirality
in addition to the sulfur atom marked (*) in formula (III), in which case
they are then present as stereoisomers. The formula (III) encompasses all
possible stereoisomers defined by their specific spatial form, such as
enantiomers, diastereomers, Z and E isomers. If, for example, one or more
alkenyl groups are present, there may be diastereomers (Z and E isomers).
If, for example, one or more asymmetric carbon atoms are present, there
may be enantiomers and diastereomers. Stereoisomers may be obtained from
the mixtures resulting from the preparation using customary separation
methods, for example by chromatographic separation techniques. It is also
possible to prepare stereoisomers selectively by using stereoselective
reactions employing optically active starting materials and/or
auxiliaries. Accordingly, the invention also relates to all stereoisomers
embraced by the formula (III) but not shown in their specific stereoform,
and to their mixtures.

[0187] If, for example, one or more alkenyl groups are present, there may
be diastereomers (Z and E isomers).

[0188] If, for example, one or more asymmetric carbon atoms are present,
there may be enantiomers and diastereomers.

[0189] Such stereoisomers may be obtained from the mixtures resulting from
the preparation using customary separation methods, for example by
chromatographic separation techniques. It is also possible to prepare
stereoisomers selectively by using stereoselective reactions employing
optically active starting materials and/or auxiliaries. Accordingly, the
invention also relates to all stereoisomers embraced by the formula (I)
but not shown in their specific stereoform, and to their mixtures.

[0190] What is meant by the "inert solvents" referred to in the above
process variants are in each case solvents which are inert under the
particular reaction conditions but need not be inert under all reaction
conditions.

[0191] The following acids are suitable for preparing the acid addition
salts of the compounds of the formula (I):

[0192] hydrohalic acids, such as hydrochloric acid or hydrobromic acid,
furthermore phosphoric acid, nitric acid, sulfuric acid, mono- or
bifunctional carboxylic acids and hydroxycarboxylic acids, such as acetic
acid, maleic acid, succinic acid, fumaric acid, tartaric acid, citric
acid, salicylic acid, sorbic acid, or lactic acid, and also sulfonic
acids, such as p-toluenesulfonic acid and 1,5-naphthalenedisulfonic acid.
The acid addition compounds of the formula (I) can be obtained in a
simple manner by the customary methods for forming salts, for example by
dissolving a compound of the formula (I) in a suitable organic solvent,
such as, for example, methanol, acetone, methylene chloride or benzene,
and adding the acid at temperatures of from 0 to 100° C., and they
can be isolated in a known manner, for example by filtration, and, if
appropriate, purified by washing with an inert organic solvent.

[0193] The base addition salts of the compounds of the formula (I) are
preferably prepared in inert polar solvents, such as, for example, water,
methanol or acetone, at temperatures of from 0 to 100° C. Examples
of bases which are suitable for the preparation of the salts according to
the invention are alkali metal carbonates, such as potassium carbonate,
alkali metal hydroxides and alkaline earth metal hydroxides, for example
NaOH or KOH, alkali metal hydrides and alkaline earth metal hydrides, for
example NaH, alkali metal alkoxides and alkaline earth metal alkoxides,
for example sodium methoxide or potassium tert-butoxide, or ammonia,
ethanolamine or quaternary ammonium hydroxide of the formula
[NRR'R''R'''].sup.+ OH.sup.-.

[0194] Collections of compounds of the formula (I) and/or their salts
which can be synthesized in accordance with the abovementioned reactions
can also be prepared in a parallelized manner, which can be effected
manually or in a partly or fully automated manner. Here, it is possible
for example to automate the procedure of the reaction, the work-up or the
purification of the products or intermediates. In total, this is
understood as meaning a procedure as described for example by D. Tiebes
in Combinatorial Chemistry--Synthesis, Analysis, Screening (Editor
Gunther Jung), Wiley 1999, on pages 1 to 34.

[0195] A number of commercially available apparatuses can be used for the
parallelized reaction procedure and work-up, for example Calpyso reaction
blocks from Barnstead International, Dubuque, Iowa 52004-0797, USA, or
reaction stations from Radleys, Shirehill, Saffron Walden, Essex, CB 11
3AZ, England or MuItiPROBE Automated Workstations from Perkin Elmar,
Waltham, Mass. 02451, USA. Chromatographic apparatuses, for example from
ISCO, Inc., 4700 Superior Street, Lincoln, Nebr. 68504, USA, are
available, inter alia, for the parallelized purification of compounds of
the formula (I) and their salts or of intermediates generated in the
course of the preparation.

[0196] The apparatuses listed lead to a modular procedure in which the
individual passes are automated, but manual operations must be carried
out between the passes. This can be circumvented by the use of partly or
fully integrated automation systems, where the relevant automation
modules are operated by, for example, robots. Such automation systems can
be obtained for example from Caliper, Hopkinton, Mass. 01748, USA.

[0197] The performance of individual, or a plurality of, synthesis steps
can be aided by the use of polymer-supported reagents/scavenger resins.
The specialist literature describes a series of experimental protocols,
for example in ChemFiles, Vol. 4, No. 1, Polymer-Supported Scavengers and
Reagents for Solution-Phase Synthesis (Sigma-Aldrich).

[0198] Besides the methods described herein, the preparation of compounds
of the formula (I) and their salts can be effected fully or in part by
solid-phase-supported methods. For this purpose, individual
intermediates, or all intermediates, of the synthesis or of a synthesis
adapted to the relevant procedure are bound to a synthesis resin.
Solid-phase-supported synthesis methods are described sufficiently in the
specialist literature, for example Barry A. Bunin in "The Combinatorial
Index", Academic Press, 1998 and Combinatorial Chemistry--Synthesis,
Analysis, Screening (Editor Gunther Jung), Wiley, 1999. The use of
solid-phase-supported synthesis methods permits a series of protocols
known from the literature, which, again, can be carried out manually or
in an automated manner. For example, the reactions can be carried out by
means of IRORI technology in microreactors from Nexus Biosystems, 12140
Community Road, Poway, Calif. 92064, USA.

[0199] Carrying out individual or a plurality of synthesis steps, both on
a solid and in the liquid phase, can be aided by the use of microwave
technology. A series of experimental protocols are described in the
specialist literature, for example in Microwaves in Organic and Medicinal
Chemistry (Editors C. O. Kappe and A. Stadler), Wiley, 2005.

[0200] The preparation in accordance with the processes described herein
generates compounds of the formula (I) and their salts in the form of
substance collections, which are referred to as libraries. The present
invention also relates to libraries which comprise at least two compounds
of the formula (I) and their salts.

[0201] On account of their herbicidal and plant growth regulatory
properties, the active compounds can also be used for controlling harmful
plants in crops of known plants or genetically modified plants which are
yet to be developed. As a rule, the transgenic plants are distinguished
by particularly advantageous properties, for example by resistances to
certain pesticides, primarily certain herbicides, resistances to plant
diseases or pathogens of plant diseases, such as certain insects or
microorganisms such as fungi, bacteria or viruses. Other particular
properties relate, for example, to the harvested material with respect to
quantity, quality, storability, composition and specific ingredients. For
example, transgenic plants with increased starch content or modified
quality of the starch or those with a different fatty acid composition of
the harvested material are known. Further particular properties can lie
in a tolerance or resistance to abiotic stress factors, for example heat,
cold, drought, salt and ultraviolet radiation.

[0202] Preference is given to using the compounds of the formula (I)
according to the invention or their salts in economically important
transgenic crops of useful plants and ornamental plants, for example of
cereals such as wheat, barley, rye, oats, millet, rice, manioc and corn,
or else crops of sugarbeet, cotton, soybean, rapeseed, potatoes,
tomatoes, peas and other vegetable varieties.

[0203] Preferably, the compounds of the formula (I) can be used as
herbicides in crops of useful plants which are resistant to, or have been
rendered genetically resistant to, the phytotoxic effects of the
herbicides.

[0214] Numerous molecular biological techniques with which new transgenic
plants with modified properties can be produced are known in principle;
see e.g. I. Potrykus and G. Spangenberg (eds.) Gene Transfer to Plants,
Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg or
Christou, "Trends in Plant Science" 1 (1996) 423-431.

[0215] For genetic manipulations of this kind, nucleic acid molecules
which permit a mutagenesis or a sequence modification by recombination of
DNA sequences can be introduced into plasmids. For example, with the help
of standard methods, it is possible to carry out base exchanges, to
remove part sequences or to add natural or synthetic sequences. For
joining the DNA fragments to one another, adaptors or linkers may be
added to the fragments, see e.g. Sambrook et al., 1989, Molecular
Cloning, A Laboratory Manual, 2nd edition, Cold Spring Harbor Laboratory
Press, Cold Spring Harbor, N.Y.; or Winnacker "Gene and Klone [Genes and
Clones]", VCH Weinheim 2nd edition, 1996.

[0216] The preparation of plant cells with reduced activity of a gene
product can be achieved, for example, through the expression of at least
one corresponding antisense-RNA, a sense-RNA to achieve a cosuppression
effect or the expression of at least one correspondingly constructed
ribozyme which specifically cleaves transcripts of the aforementioned
gene product.

[0217] To this end, it is possible to use firstly DNA molecules which
encompass the entire coding sequence of a gene product including any
flanking sequences which may be present, and also DNA molecules which
only encompass parts of the coding sequence, it being necessary for these
parts to be long enough to bring about an antisense effect in the cells.
Also possible is the use of DNA sequences which have a high degree of
homology to the coding sequences of a gene product but are not entirely
identical thereto.

[0218] During the expression of nucleic acid molecules in plants, the
synthesized protein can be localized in any compartment of the plant
cell. However, in order to achieve localization in a certain compartment,
it is possible, for example, to link the coding region with DNA sequences
which ensure localization in a certain compartment. Sequences of this
type are known to the person skilled in the art (see, for example, Braun
et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad.
Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991),
95-106). The expression of the nucleic acid molecules can also take place
in the organelles of the plant cells.

[0219] The transgenic plant cells can be regenerated by known techniques
to give whole plants. In principle, the transgenic plants may be plants
of any desired plant species, i.e. either monocotyledonous or
dicotyledonous plants.

[0220] Transgenic plants are thus obtainable which have modified
properties as a result of overexpression, suppression or inhibition of
homologous (=natural) genes or gene sequences or expression of
heterologous (=foreign) genes or gene sequences.

[0221] It is preferred to employ the compounds (I) according to the
invention in transgenic crops which are resistant to growth regulators
such as, for example, dicamba, or against herbicides which inhibit
essential plant enzymes, for example acetolactate synthases (ALS), EPSP
synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases
(HPPD), or against herbicides from the group of the sulfonylureas,
glyphosates, glufosinates or benzoylisoxazoles and analogous active
compounds or against any combinations of these active compounds.

[0222] The compounds according to the invention can be particularly
preferably used in transgenic crop plants which are resistant to a
combination of glyphosates and glufosinates, glyphosates and
sulfonylureas or imidazolinones. The compounds according to the invention
can very particularly preferably be used in transgenic crop plants such
as e.g. corn or soybean with the tradename or the name Optimum®
GAT® (glyphosate ALS tolerant).

[0223] When the active compounds according to the invention are used in
transgenic crops, effects are frequently observed--in addition to the
effects on harmful plants which can be observed in other crops--which are
specific for the application in the transgenic crop in question, for
example a modified or specifically widened spectrum of weeds which can be
controlled, modified application rates which may be employed for
application, preferably good combinability with the herbicides to which
the transgenic crop is resistant, and an effect on growth and yield of
the transgenic crop plants.

[0224] The invention therefore also relates to the use of the compounds of
the formula (I) according to the invention as herbicides for controlling
harmful plants in transgenic crop plants.

[0225] The compounds according to the invention can be used in the form of
wettable powders, emulsifiable concentrates, sprayable solutions, dusting
products or granules in the customary formulations. The invention
therefore also provides herbicides and plant growth-regulating
compositions which comprise the compounds according to the invention.

[0229] Based on these formulations, it is also possible to prepare
combinations with other pesticidally active compounds, such as, for
example, insecticides, acaricides, herbicides, fungicides, and also with
safeners, fertilizers and/or growth regulators, for example in the form
of a ready mix or as a tank mix.

[0230] Wettable powders are preparations which can be dispersed uniformly
in water and, as well as the active compound, apart from a diluent or
inert substance, also comprise surfactants of the ionic and/or nonionic
type (wetting agents, dispersants), for example polyoxyethylated
alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty
amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates,
alkylbenzenesulfonates, sodium lignosulfonate, sodium
2,2'-dinaphthylmethane-6,6'-disulfonate, sodium
dibutylnaphthalenesulfonate or else sodium oleylmethyltauride. To prepare
the wettable powders, the active herbicidal ingredients are ground
finely, for example in customary apparatus such as hammer mills, blower
mills and air-jet mills, and simultaneously or subsequently mixed with
the formulation assistants.

[0232] Dusting products are obtained by grinding the active compound with
finely divided solid substances, for example talc, natural clays such as
kaolin, bentonite and pyrophyllite, or diatomaceous earth.

[0233] Suspension concentrates may be water- or oil-based. They may be
prepared, for example, by wet grinding by means of commercial bead mills
and optional addition of surfactants as have, for example, already been
listed above for the other formulation types.

[0234] Emulsions, for example oil-in-water emulsions (EW), can be
prepared, for example, by means of stirrers, colloid mills and/or static
mixers using aqueous organic solvents and optionally surfactants, as
have, for example, already been listed above for the other formulation
types.

[0235] Granules can be produced either by spraying the active compound
onto adsorptive granulated inert material or by applying active compound
concentrates by means of adhesives, for example polyvinyl alcohol, sodium
polyacrylate or else mineral oils, onto the surface of carriers such as
sand, kaolinites or of granulated inert material. It is also possible to
granulate suitable active compounds in the manner customary for the
production of fertilizer granules--if desired in a mixture with
fertilizers.

[0238] For further details regarding the formulation of crop protection
compositions, see, for example, G. C. Klingman, "Weed Control as a
Science", John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J.
D. Freyer, S. A. Evans, "Weed Control Handbook", 5th Ed., Blackwell
Scientific Publications, Oxford, 1968, pages 101-103. The agrochemical
formulations contain generally from 0.1 to 99% by weight, in particular
from 0.1 to 95% by weight, of active compound of the formula (I).

[0239] In wettable powders, the active compound concentration is, for
example, from about 10 to 90% by weight; the remainder to 100% by weight
consists of customary formulation constituents. In the case of
emulsifiable concentrates, the active compound concentration may be from
about 1 to 90% by weight, preferably from 5 to 80% by weight. Dust-type
formulations contain from 1 to 30% by weight of active compound,
preferably usually from 5 to 20% by weight of active compound; sprayable
solutions contain from about 0.05 to 80% by weight, preferably from 2 to
50% by weight of active compound. In water-dispersible granules, the
active compound content depends partly on whether the active compound is
present in solid or liquid form and which granulation assistants,
fillers, etc. are used. In the granules dispersible in water, the content
of active compound is, for example, between 1 and 95% by weight,
preferably between 10 and 80% by weight.

[0240] In addition, the specified active compound formulations optionally
comprise the adhesives, wetting agents, dispersants, emulsifiers,
penetration agents, preservatives, antifreezes and solvents, fillers,
carriers and colorants, antifoams, evaporation inhibitors and agents
which influence the pH and the viscosity that are customary in each case.

[0241] The compounds of the formula (I) or their salts can be used as such
or combined in the form of their preparations (formulations) with other
pesticidally active substances, such as, for example, insecticides,
acaricides, nematicides, herbicides, fungicides, safeners, fertilizers
and/or growth regulators, e.g. as ready mix or as tank mixes.

[0242] Combination partners which can be used for the compounds of the
formula (I) according to the invention in mixture formulations or in the
tank mix are, for example, known active compounds which are based on an
inhibition of, for example, acetolactate synthase,
acetyl-coenzyme-A-carboxylase, cellulose synthase,
enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase,
p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I,
photosystem II, protoporphyrinogen oxidase, as described, for example, in
Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 14th edition,
The British Crop Protection Council and the Royal Soc. of Chemistry, 2003
and literature cited therein. Known herbicides or plant growth regulators
which can be combined with the compounds according to the invention are,
for example, the following active compounds (the compounds are designated
either with the "common name" in accordance with the International
Organization for Standardization (ISO) or with the chemical name or with
the code number) and always encompass all of the application forms such
as acids, salts, esters and isomers such as stereoisomers and optical
isomers. Here, by way of example, one and sometimes also more application
forms are specified:

[0244] Of particular interest is the selective control of harmful plants
in crops of useful plants and ornamental plants. Although the compounds
of the formula (I) according to the invention already have very good to
adequate selectivity in many crops, it is in principle possible, in some
crops and primarily also in the case of mixtures with other herbicides
which are less selective, for phytotoxicities on the crop plants to
occur. In this connection, combinations of compounds of the formula (I)
according to the invention are of particular interest which comprise the
compounds of the formula (I) or their combinations with other herbicides
or pesticides and safeners. The safeners which are used in an
antidotically effective content reduce the phytotoxic side-effects of the
herbicides/pesticides used, e.g. in economically important crops such as
cereals (wheat, barley, rye, corn, rice, millet), sugarbeet, sugarcane,
rapeseed, cotton and soybean, preferably cereals. The following groups of
compounds are suitable, for example, as safeners for the compounds (I)
alone or else in their combinations with further pesticides:

[0245] S1) Compounds of the formula (S1),

##STR00030##

where the symbols and indices have the following meanings: [0246] nA
is a natural number from 0 to 5, preferably 0 to 3; [0247] RA1
is halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, nitro or
(C1-C4)-haloalkyl; [0248] WA is an unsubstituted or
substituted divalent heterocyclic radical from the group of the partially
unsaturated or aromatic five-ring heterocycles having 1 to 3 heteroring
atoms from the group consisting of N and O, where at least one N atom and
at most one O atom is present in the ring, preferably a radical from the
group (WA1) to (WA4),

[0248] ##STR00031## [0249] mA is 0 or 1; [0250] RA2 is
ORA3, SRA3 or NRA3RA4 or a
saturated or unsaturated 3- to 7-membered heterocycle with at least one N
atom and up to 3 heteroatoms, preferably from the group consisting of O
and S, which is bonded to the carbonyl group in (S1) via the N atom and
is unsubstituted or substituted by radicals from the group consisting of
(C1-C4)-alkyl, (C1-C4)-alkoxy or optionally
substituted phenyl, preferably a radical of the formula ORA3,
NHRA4 or N(CH3)2, in particular of the formula
ORA3; [0251] RA3 is hydrogen or an unsubstituted or
substituted aliphatic hydrocarbon radical, preferably having in total 1
to 18 carbon atoms; [0252] RA4 is hydrogen,
(C1-C6)-alkyl, (C1-C6)-alkoxy or substituted or
unsubstituted phenyl; [0253] RA5 is H, (C1-C8)-alkyl,
(C1-C8)-haloalkyl,
(C1-C4)-alkoxy-(C1-C8)-alkyl, cyano or
COORA9, in which RA9 is hydrogen,
(C1-C8)-alkyl, (C1-C8)-haloalkyl,
(C1-C4)-alkoxy-(C1-C4)-alkyl,
(C1-C6)-hydroxyalkyl, (C3-C12)-cycloalkyl or
tri-(C1-C4)-alkylsilyl; [0254] RA6, RA7,
RA8 are identical or different, hydrogen,
(C1-C8)-alkyl, (C1-C8)-haloalkyl,
(C3-C12)-cycloalkyl or substituted or unsubstituted phenyl;
preferably: [0255] a) compounds of the
dichlorophenylpyrazoline-3-carboxylic acid type (S1a), preferably
compounds such as
1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxy-
lic acid, ethyl
1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxy-
late (S1-1) ("mefenpyr-diethyl"), and related compounds, as described in
WO-A-91/07874; [0256] b) derivatives of dichlorophenylpyrazolecarboxylic
acid (S1b), preferably compounds such as ethyl
1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate (S1-2), ethyl
1-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylate (S1-3), ethyl
1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)pyrazole-3-carboxylate (S1-4)
and related compounds, as described in EP-A-333 131 and EP-A-269 806;
[0257] c) derivatives of 1,5-diphenylpyrazole-3-carboxylic acid
(S1c), preferably compounds such as ethyl
1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-5), methyl
1-(2-chlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-6) and related
compounds, as described, for example, in EP-A-268554; [0258] d) compounds
of the triazolecarboxylic acid type (S1d), preferably compounds such
as fenchlorazole(-ethyl), i.e. ethyl
1-(2,4-dichlorophenyl)-5-trichloro-methyl-(1H)-1,2,4-triazole-3-carboxyla-
te (51-7), and related compounds, as described in EP-A-174 562 and
EP-A-346 620; [0259] e) compounds of the 5-benzyl- or
5-phenyl-2-isoxazoline-3-carboxylic acid type or of the
5,5-diphenyl-2-isoxazoline-3-carboxylic acid type (S1e), preferably
compounds such as ethyl
5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate (S1-8) or ethyl
5-phenyl-2-isoxazoline-3-carboxylate (S1-9) and related compounds, as
described in WO-A-91/08202, or 5,5-diphenyl-2-isoxazoline-carboxylic acid
(S1-10) or ethyl 5,5-diphenyl-2-isoxazolinecarboxylate (S1-11)
("isoxadifen-ethyl") or n-propyl 5,5-diphenyl-2-isoxazolinecarboxylate
(S1-12) or of the ethyl
5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate type (S1-13), as
described in the patent application WO-A-95/07897. S2) Quinoline
derivatives of the formula (S2),

##STR00032##

[0259] where the symbols and indices have the following meanings: [0260]
RB1 is halogen, (C1-C4)-alkyl,
(C1-C4)-alkoxy, nitro or (C1-C4)-haloalkyl; [0261]
nB is a natural number from 0 to 5, preferably 0 to 3; [0262]
RB2 is ORB3, SRB3 or
NRB3RB4 or a saturated or unsaturated 3- to
7-membered heterocycle having at least one N atom and up to 3
heteroatoms, preferably from the group consisting of O and S, which is
joined to the carbonyl group in (S2) via the N atom and is unsubstituted
or substituted by radicals from the group consisting of
(C1-C4)-alkyl, (C1-C4)-alkoxy or optionally
substituted phenyl, preferably a radical of the formula ORB3,
NHRB4 or N(CH3)2, in particular of the formula
ORB3; [0263] RB3 is hydrogen or an unsubstituted or
substituted aliphatic hydrocarbon radical, preferably having in total 1
to 18 carbon atoms; [0264] RB4 is hydrogen,
(C1-C6)-alkyl, (C1-C6)-alkoxy or substituted or
unsubstituted phenyl; [0265] TB is a (C1 or C2)-alkanediyl
chain which is unsubstituted or substituted by one or two
(C1-C4)-alkyl radicals or by
[(C1-C3)-alkoxy]carbonyl; preferably: [0266] a) compounds of
the 8-quinolinoxyacetic acid type (S2a), preferably 1-methylhexyl
(5-chloro-8-quinolinoxy)acetate ("cloquintocet-mexyl") (S2-1),
1,3-dimethylbut-1-yl (5-chloro-8-quinolinoxy)acetate(S2-2),
4-allyloxybutyl (5-chloro-8-quinolinoxy)acetate(S2-3),
1-allyloxyprop-2-yl (5-chloro-8-quinolinoxy)acetate(S2-4), ethyl
(5-chloro-8-quinolinoxy)acetate(S2-5), methyl
(5-chloro-8-quinolinoxy)acetate(S2-6), allyl
(5-chloro-8-quinolinoxy)acetate(S2-7), 2-(2-propylideneiminoxy)-1-ethyl
(5-chloro-8-quinolinoxy)acetate(S2-8), 2-oxoprop-1-yl
(5-chloro-8-quinolinoxy)acetate(S2-9) and related compounds, as described
in EP-A-86 750, EP-A-94 349 and EP-A-191 736 or EP-A-0 492 366, and also
(5-chloro-8-quinolinoxy)acetic acid (S2-10), its hydrates and salts, for
example its lithium, sodium, potassium, calcium, magnesium, aluminum,
iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts, as
described in WO-A-2002/34048; [0267] b) compounds of the
(5-chloro-8-quinolinoxy)malonic acid type (S2b), preferably
compounds such as diethyl (5-chloro-8-quinolinoxy)malonate, diallyl
(5-chloro-8-quinolinoxy)malonate, methyl ethyl
(5-chloro-8-quinolinoxy)-malonate and related compounds, as described in
EP-A-0 582 198. S3) Compounds of the formula (S3)

[0276] in which the symbols and indices have the following meanings:
[0277] XD is CH or N; [0278] RD1 is
CO--NRD5RD6 or NHCO--RD7; [0279]
RD2 is halogen, (C1-C4)-haloalkyl,
(C1-C4)-haloalkoxy, nitro, (C1-C4)-alkyl,
(C1-C4)-alkoxy, (C1-C4)-alkylsulfonyl,
(C1-C4)-alkoxycarbonyl or (C1-C4)-alkylcarbonyl;
[0280] RD3 is hydrogen, (C1-C4)-alkyl,
(C2-C4)-alkenyl or (C2-C4)-alkynyl; [0281]
RD4 is halogen, nitro, (C1-C4)-alkyl,
(C1-C4)-haloalkyl, (C1-C4)-haloalkoxy,
(C3-C6)-cycloalkyl, phenyl, (C1-C4)-alkoxy, cyano,
(C1-C4)-alkylthio, (C1-C4)-alkyl-sulfinyl,
(C1-C4)-alkylsulfonyl, (C1-C4)-alkoxycarbonyl or
(C1-C4)-alkylcarbonyl; [0282] RD5 is hydrogen,
(C1-C6)-alkyl, (C3-C6)-cycloalkyl,
(C2-C6)-alkenyl, (C2-C6)-alkynyl,
(C5-C6)-cycloalkenyl, phenyl or 3- to 6-membered heterocyclyl
comprising VD heteroatoms from the group consisting of nitrogen,
oxygen and sulfur, where the seven last-mentioned radicals are
substituted by vD substituents from the group consisting of halogen,
(C1-C6)-alkoxy, (C1-C6)-haloalkoxy,
(C1-C2)-alkylsulfinyl, (C1-C2)-alkylsulfonyl,
(C3-C6)-cycloalkyl, (C1-C4)-alkoxycarbonyl,
(C1-C4)-alkylcarbonyl and phenyl and, in the case of cyclic
radicals, also (C1-C4)-alkyl and (C1-C4)-haloalkyl;
[0283] RD6 is hydrogen, (C1-C6)-alkyl,
(C2-C6)-alkenyl or (C2-C6)-alkynyl, where the three
last-mentioned radicals are substituted by vD radicals from the
group consisting of halogen, hydroxyl, (C1-C4)-alkyl,
(C1-C4)-alkoxy and (C1-C4)-alkylthio, or [0284]
RD5 and RD6 together with the nitrogen atom carrying
them form a pyrrolidinyl or piperidinyl radical; [0285] RD7 is
hydrogen, (C1-C4)-alkylamino, di-(C1-C4)-alkylamino,
(C1-C6)-alkyl, (C3-C6)-cycloalkyl, where the 2
last-mentioned radicals are substituted by vD substituents from the
group consisting of halogen, (C1-C4)-alkoxy,
(C1-C6)-haloalkoxy and (C1-C4)-alkylthio and, in the
case of cyclic radicals, also (C1-C4)-alkyl and
(C1-C4)-haloalkyl; [0286] nD is 0, 1 or 2; [0287] mD
is 1 or 2; [0288] vD is 0, 1, 2 or 3; [0289] of which preference is
given to compounds of the N-acylsulfonamide type, for example of the
following formula (S4a), which are known, for example, from WO-A-97/45016

##STR00035##

[0289] in which [0290] RD7 is (C1-C6)-alkyl,
(C3-C6)-cycloalkyl, where the 2 last-mentioned radicals are
substituted by VD substituents from the group consisting of halogen,
(C1-C4)-alkoxy, (C1-C6)-haloalkoxy and
(C1-C4)-alkylthio and, in the case of cyclic radicals, also
(C1-C4)-alkyl and (C1-C4)-haloalkyl; [0291]
RD4 is halogen, (C1-C4)-alkyl,
(C1-C4)-alkoxy, CF3; [0292] mD is 1 or 2; [0293]
vD is 0, 1, 2 or 3; and [0294] acylsulfamoylbenzamides, e.g. of the
following formula (S4b), which are known, for example, from
WO-A-99/16744,

##STR00036##

[0294] e.g. those in which RD5=cyclopropyl and
(RD4)=2-OMe ("cyprosulfamide", S4-1), RD5=cyclopropyl
and (RD4)=5-Cl-2-OMe (S4-2), RD5=ethyl and
(RD4)=2-OMe (S4-3), RD5=isopropyl and
(RD4)=5-Cl-2-OMe (S4-4) and RD5=isopropyl and
(RD4)=2-OMe (S4-5), and [0295] compounds of the
N-acylsulfamoylphenylurea type of the formula (S4c), which are
known, for example, from EP-A-365484,

[0304] in which the symbols and the indices have the following meanings:
[0305] RE1, RE2 independently of one another are
halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy,
(C1-C4)-haloalkyl, (C1-C4)-alkylamino,
di-(C1-C4)-alkylamino, nitro; [0306] AE is
COORE3 or COSRE4[0307] RE3, RE4
independently of one another are hydrogen, (C1-C4)-alkyl,
(C2-C6)-alkenyl, (C2-C4)-alkynyl, cyanoalkyl,
(C1-C4)-haloalkyl, phenyl, nitrophenyl, benzyl, halobenzyl,
pyridinylalkyl and alkylammonium, [0308] nE1 is 0 or 1 [0309]
nE2, nE3 independently of one another are 0, 1 or 2,
preferably: [0310] diphenylmethoxyacetic acid, [0311] ethyl
diphenylmethoxyacetate, [0312] methyl diphenylmethoxyacetate(CAS Reg. No.
41858-19-9) (S7-1). [0313] S8) Compounds of the formula (S8), as
described in WO-A-98/27049

##STR00039##

[0313] in which [0314] XF is CH or N, [0315] nF if
XF═N, is an integer from 0 to 4 and [0316] if XF═CH,
is an integer from 0 to 5, [0317] RF1 is halogen,
(C1-C4)-alkyl, (C1-C4)-haloalkyl,
(C1-C4)-alkoxy, (C1-C4)-haloalkoxy, nitro,
(C1-C4)-alkylthio, (C1-C4)-alkylsulfonyl,
(C1-C4)-alkoxycarbonyl, optionally substituted phenyl,
optionally substituted phenoxy, [0318] RF2 is hydrogen or
(C1-C4)-alkyl, [0319] RF3 is hydrogen,
(C1-C8)-alkyl, (C2-C4)-alkenyl,
(C2-C4)-alkynyl, or aryl, where each of the aforementioned
C-containing radicals is unsubstituted or substituted by one or more,
preferably up to three, identical or different radicals from the group
consisting of halogen and alkoxy, or salts thereof, preferably compounds
in which [0320] XF is CH, [0321] nF is an integer from 0 to 2,
[0322] RF1 is halogen, (C1-C4)-alkyl,
(C1-C4)-haloalkyl, (C1-C4)-alkoxy,
(C1-C4)-haloalkoxy, [0323] RF2 is hydrogen or
(C1-C4)-alkyl, [0324] RF3 is hydrogen,
(C1-C8)-alkyl, (C2-C4)-alkenyl,
(C2-C4)-alkynyl, or aryl, where each of the aforementioned
C-containing radicals is unsubstituted or substituted by one or more,
preferably up to three, identical or different radicals from the group
consisting of halogen and alkoxy, or salts thereof. [0325] S9) Active
compounds from the class of the 3-(5-tetrazolylcarbonyl)-2-quinolones
(S9), e.g. [0326]
1,2-dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS
Reg. No. 219479-18-2),
1,2-dihydro-4-hydroxy-1-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS
Reg. No. 95855-00-8), as described in WO-A-1999/000020. [0327] S10)
Compounds of the formulae (S10a) or (S10b) [0328] as described
in WO-A-2007/023719 and WO-A-2007/023764

##STR00040##

[0328] in which [0329] RG1 is halogen, (C1-C4)-alkyl,
methoxy, nitro, cyano, CF3, OCF3[0330] YG, ZG
independently of one another are O or S, [0331] nG is an integer
from 0 to 4, [0332] RG2 is (C1-C16)-alkyl,
(C2-C6)-alkenyl, (C3-C6)-cycloalkyl, aryl; benzyl,
halobenzyl, [0333] RG3 is hydrogen or (C1-C6)-alkyl.
[0334] S11) Active compounds of the oxyimino compound type (S11), which
are known as seed dressings, such as, for example, [0335] "oxabetrinil"
((Z)-1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (S11-1), which is
known as seed dressing safener for millet against metolachlor damage,
[0336] "fluxofenim" (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanone
O-(1,3-dioxolan-2-ylmethyl)oxime) (S11-2), which is known as seed
dressing safener for millet against metolachlor damage, and [0337]
"cyometrinil" or "CGA-43089" ((Z)-cyanomethoxyimino(phenyl)acetonitrile)
(S11-3), which is known as seed dressing safener for millet against
metolachlor damage. [0338] S12) Active compounds from the class of the
isothiochromanones (S12), such as, for example, methyl
[(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]acetate (CAS Reg. No.
205121-04-6) (S12-1) and related compounds from WO-A-1998/13361. [0339]
S13) One or more compounds from group (S13): [0340] "naphthalic
anhydride" (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is
known as seed dressing safener for corn against thiocarbamate herbicide
damage, [0341] "fenclorim" (4,6-dichloro-2-phenylpyrimidine) (S13-2),
which is known as safener for pretilachlor in sown rice, [0342]
"flurazole" (benzyl
2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S13-3), which is
known as seed dressing safener for millet against alachlor and
metolachlor damage, [0343] "CL 304415" (CAS Reg. No. 31541-57-8)
(4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4) from
American Cyanamid, which is known as safener for corn against
imidazolinone damage, [0344] "MG 191" (CAS Reg. No. 96420-72-3)
(2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, which
is known as safener for corn, [0345] "MG-838" (CAS Reg. No. 133993-74-5)
(2-propenyl 1-oxa-4-azaspiro[4.5]decane-4-carbodithioate) (S13-6) from
Nitrokemia, [0346] "disulfoton" (0,0-diethyl S-2-ethylthioethyl
phosphorodithioate) (S13-7), [0347] "dietholate" (0,0-diethyl O-phenyl
phosphorothioate) (S13-8), [0348] "mephenate" (4-chlorophenyl
methylcarbamate) (S13-9). [0349] S14) Active compounds which, besides a
herbicidal effect against harmful plants, also have safener effect on
crop plants such as rice, such as, for example, "dimepiperate" or "MY-93"
(S-1-methyl-1-phenylethyl piperidine-1-carbothioate), which is known as
safener for rice against molinate herbicide damage, [0350] "daimuron" or
"SK 23" (1-(1-methyl-1-phenylethyl)-3-p-tolylurea), which is known as
safener for rice against imazosulfuron herbicide damage, [0351]
"cumyluron"="JC-940"
(3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenyl-ethyl)urea, see
JP-A-60087254), which is known as safener for rice against some herbicide
damage, [0352] "methoxyphenone" or "NK 049"
(3,3'-dimethyl-4-methoxybenzophenone), which is known as safener for rice
against some herbicide damage, [0353] "CSB"
(1-bromo-4-(chloromethylsulfonyl)benzene) from Kumiai, (CAS Reg. No.
54091-06-4), which is known as safener against some herbicide damage in
rice. [0354] S15) Active compounds which are primarily used as
herbicides, but also have safener effect on crop plants, for example
[0355] (2,4-dichlorophenoxy)acetic acid (2,4-D), [0356]
(4-chlorophenoxy)acetic acid, [0357]
(R,S)-2-(4-chloro-o-tolyloxy)propionic acid (mecoprop), [0358]
4-(2,4-dichlorophenoxy)butyric acid (2,4-DB), [0359]
(4-chloro-o-tolyloxy)acetic acid (MCPA), [0360]
4-(4-chloro-o-tolyloxy)butyric acid, [0361] 4-(4-chlorophenoxy)butyric
acid, [0362] 3,6-dichloro-2-methoxybenzoic acid (dicamba), [0363]
1-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate
(lactidichlor-ethyl).

[0364] Some of the safeners are already known as herbicides and thus,
besides the herbicidal effect in respect of harmful plants, at the same
time also develop a protective effect in respect of the crop plants.

[0365] The weight ratios of herbicide (mixture) to safener generally
depend on the application rate of herbicide and the effectiveness of the
particular safener and can vary within wide limits, for example in the
range from 200:1 to 1:200, preferably 100:1 to 1:100, in particular 20:1
to 1:20. The safeners can be formulated analogously to the compounds of
the formula (I) or mixtures thereof with further herbicides/pesticides
and can be provided and applied as ready mix or tank mix with the
herbicides.

[0366] For use, the formulations present in standard commercial form are,
if appropriate, diluted in the usual manner, e.g. in the case of wettable
powders, emulsifiable concentrates, dispersions and water-dispersible
granules by means of water. Dust-like preparations, soil and scatter
granules, and also sprayable solutions are usually no longer diluted with
further inert substances prior to use.

[0367] The required application rate of the compounds of the formula (I)
varies inter alia with the external conditions such as temperature,
humidity, the type of herbicide used. It can fluctuate within wide
limits, e.g. between 0.001 and 10.0 kg/ha or more of active substance,
but is preferably between 0.005 and 5 kg/ha.

[0368] The present invention is illustrated in more detail by reference to
the examples below, although these do not limit the present invention in
any way.

SYNTHESIS EXAMPLES

[0369] A number of synthesis examples of compounds of the formula (I) or
their salts are described in an exemplary manner below.

(1) 2-[(2,5-Dimethylbenzypsulfanyl]-1,3-oxazole (Ex. 130)

[0370] 1,3-Oxazole-2(3H)-thione (0.500 g, 5 mmol, prepared according to WO
03/006442 A) is initially charged in 15 ml of acetonitrile. With ice-bath
cooling, 1,8-diazabicyclo-(5.4.0)undec-7-ene (DBU, 0.81 ml, 5 mmol) is
added dropwise. The mixture is stirred at 25° C. for 10 minutes. A
solution of 2-(bromomethyl)-1,4-dimethylbenzene (0.984 g, 5 mmol),
dissolved in acetonitrile, is added dropwise. The mixture is stirred at
25° C. for a further 4 hours and allowed to stand overnight. For
work-up, the reaction mixture is added to water and extracted twice with
dichloromethane, and the extract is then washed with water and finally
with saturated NaCl solution. The combined organic phases are dried over
magnesium sulfate, filtered off and concentrated. The crude product is
purified chromatographically (heptane:ethyl acetate, gradient 10:0 to
8:2). This gives 0.78 g of product (68.3% of theory).

[0372] 1,3-Oxazole-2(3H)-thione (0.500 g, 5 mmol, prepared according to WO
03/006442 A) is initially charged in 10 ml of acetonitrile. With ice-bath
cooling, 1,8-diazabicyclo-(5.4.0)undec-7-ene (DBU, 0.812 ml, 5 mmol) is
added dropwise. The mixture is stirred at 25° C. for 10 minutes. A
solution of 2-(bromomethyl)-1,3-dichlorobenzene (1.186 g, 5 mmol),
dissolved in acetonitrile, is added dropwise. The mixture is stirred at
25° C. for a further 5 hours and allowed to stand overnight. For
work-up, the reaction mixture is added to water and extracted twice with
dichloromethane, and the extract is then washed with water and finally
with saturated NaCl solution. The combined organic phases are dried over
magnesium sulfate, filtered off and concentrated. The crude product is
purified chromatographically (heptane:ethyl acetate, gradient 10:0 to
7:3). This gives 0.66 g of product (48.7% of theory).

[0374] Under an atmosphere of argon,
2-[(2,6-dichlorobenzypsulfanyl]-1,3-oxazole (0.298 g, 1 mmol) is
initially charged in 50 ml of dichloromethane. With stirring and
ice-cooling, 3-chloroperbenzoic acid (0.257 g, 1 mmol, 77% pure) is then
added a little at a time, and the mixture is stirred at 0° C. for
a further 6 hours. For work-up, the reaction mixture is washed twice with
2-molar sodium hydroxide solution, then with water and finally with
saturated NaCl solution. The combined organic phases are dried over
magnesium sulfate, filtered off and concentrated. This gives 0.290 g of
product (87% of theory).

[0377] 1,3-Oxazole-2(3H)-thione (0.500 g, 5 mmol, prepared according to WO
03/006442 A) is initially charged in 10 ml of acetonitrile. With ice-bath
cooling, 1,8-diazabicyclo-(5.4.0)undec-7-ene (DBU, 0.812 ml, 5 mmol) is
added dropwise. The mixture is stirred at 25° C. for 10 minutes. A
solution of 2-(bromomethyl)-1,3-difluorobenzene (1.024 g, 5 mmol),
dissolved in acetonitrile, is added dropwise. The mixture is stirred at
25° C. for a further 5 hours and allowed to stand overnight. For
work-up, the reaction mixture is added to water and extracted twice with
dichloromethane, and the extract is then washed with water and finally
with saturated NaCl solution. The combined organic phases are dried over
magnesium sulfate, filtered off and concentrated. The crude product is
purified chromatographically (heptane:ethyl acetate, gradient 10:0 to
8:2). This gives 0.69 g of product (58.3% of theory).

[0379] Under an atmosphere of argon,
2-[(2,6-difluorobenzyl)sulfanyl]-1,3-oxazole (0.326 g, 1 mmol) is
initially charged in 50 ml of dichloromethane. With stirring and
ice-cooling, 3-chloroperbenzoic acid (0.810 g, 3.6 mmol, 77% pure) is
then added a little at a time, and the mixture is stirred at 25°
C. for a further 6 hours and allowed to stand overnight. For work-up, the
reaction mixture is washed twice with 2-molar sodium hydroxide solution,
then with water and finally with saturated NaCl solution. The combined
organic phases are dried over magnesium sulfate, filtered off and
concentrated. This gives 0.312 g of product (75.4% of theory).

[0381] Under an atmosphere of protective gas, 1,3-oxazole-2(3H)-thione
(1.00 g, 10 mmol; prepared according to WO 03/006442 A) is initially
charged in 20 ml of acetonitrile. Iodomethane (1.544 g, 0.677 ml, 11
mmol) is added dropwise, followed by potassium carbonate (1.503 g, 11
mmol). The mixture is stirred at 25° C. for 6 hours. For work-up,
the reaction mixture is added to water and extracted twice with
dichloromethane (100 ml), and the extract is then washed with water and
finally with saturated NaCl solution. The combined organic phases are
dried over magnesium sulfate, filtered off and directly reacted further.
With stirring and ice-cooling, 3-chloro-perbenzoic acid (5.100 g, 23
mmol, 77% pure) is then added a little at a time to the resultung
dichloromethane solution, and the mixture is stirred at 25° C. for
a further 6 hours and then allowed to stand overnight. For work-up, the
reaction mixture is washed twice with 2-molar sodium hydroxide solution,
then with water and finally with saturated NaCl solution. The combined
organic phases are dried over magnesium sulfate, filtered off and
concentrated. This gives 0.820 g of product (50.7% of theory).

[0383] 2,3,6-Trichlorobenzyl bromide (0.267 g, 1 mmol) is initially
charged in ethanol (10 ml). Thiourea (0.074 g, 1 mmol) is added, and the
mixture is heated under reflux for 2 hours. The solution is then cooled
to 25° C. and 2-(methylsulfonyl)-1,3-oxazole (0.130 mg, 1 mmol) is
added, followed by potassium carbonate (0.183 g, 1 mmol). The mixture is
heated under reflux for 6 hours. For work-up, the reaction solution is
added to water and extracted with dichloromethane. The combined organic
phases are dried and concentrated. This gives 0.063 g of product (23% of
theory).

[0428] The NMR data given above were measured at 400 MHz and in CDCl3
as solvent. The chemical shift δ is stated in ppm (reference TMS).

B. Formulation Examples

[0429] a) A dust is obtained by mixing 10 parts by weight of a compound
of the formula (I) and/or a salt thereof and 90 parts by weight of talc
as inert substance and comminuting the mixture in a hammer mill. [0430]
b) A wettable powder which is readily dispersible in water is obtained by
mixing 25 parts by weight of a compound of the formula (I) and/or a salt
thereof, 64 parts by weight of kaolin-containing quartz as inert
substance, 10 parts by weight of potassium lignosulfonate and 1 part by
weight of sodium oleoylmethyltaurinate as wetting agent and dispersant,
and grinding the mixture in a pinned-disk mill. [0431] c) A readily
water-dispersible dispersion concentrate is obtained by mixing 20 parts
by weight of a compound of the formula (I) and/or a salt thereof with 6
parts by weight of alkylphenol polyglycol ether (®Triton X 207), 3
parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by
weight of paraffinic mineral oil (boiling range for example about 255 to
above 277° C.) and grinding the mixture in a ball mill to a
fineness of below 5 microns. [0432] d) An emulsifiable concentrate is
obtained from 15 parts by weight of a compound of the formula (I) and/or
a salt thereof, 75 parts by weight of cyclohexanone as solvent and 10
parts by weight of oxethylated nonylphenol as emulsifier. [0433] e)
Water-dispersible granules are obtained by mixing [0434] 75 parts by
weight of a compound of the formula (I) and/or a salt thereof, [0435] 10
parts by weight of calcium lignosulfonate, [0436] 5 parts by weight of
sodium lauryl sulfate, [0437] 3 parts by weight of polyvinyl alcohol and
[0438] 7 parts by weight of kaolin, grinding the mixture in a pinned-disk
mill, and granulating the powder in a fluidized bed by spraying on water
as granulating liquid. [0439] f) Water-dispersible granules are also
obtained by homogenizing and precomminuting, in a colloid mill, [0440]
25 parts by weight of a compound of the formula (I) and/or a salt
thereof, [0441] 5 parts by weight of sodium
2,2'-dinaphthylmethane-6,6'-disulfonate, [0442] 2 parts by weight of
sodium oleoylmethyltaurinate, [0443] 1 part by weight of polyvinyl
alcohol, [0444] 17 parts by weight of calcium carbonate and [0445] 50
parts by weight of water, subsequently grinding the mixture in a bead
mill and atomizing and drying the resulting suspension in a spray tower
by means of a single-substance nozzle.

C. Biological Examples

[0446] The compounds of the formula (I) according to the invention (and/or
their salts), hereinbelow also referred to together as "compounds
according to the invention", have excellent herbicidal efficacy against a
broad spectrum of economically important monocotyledonous and
dicotyledonous annual harmful plants. The active compounds act
efficiently even on perennial harmful plants which produce shoots from
rhizomes, root stocks and other perennial organs and which are difficult
to control.

[0447] The present invention therefore also relates to a method for
controlling unwanted plants or for regulating the growth of plants,
preferably in crops of plants, where one or more compound(s) according to
the invention is/are applied to the plants (for example harmful plants
such as monocotyledonous or dicotyledonous weeds or undesired crop
plants), to the seeds (for example grains, seeds or vegetative propagules
such as tubers or shoot parts with buds) or to the area on which the
plants grow (for example the area under cultivation). In this context,
the compounds according to the invention can be applied for example
pre-sowing (if appropriate also by incorporation into the soil),
pre-emergence or post-emergence. Specific examples may be mentioned of
some representatives of the monocotyledonous and dicotyledonous weed
flora which can be controlled by the compounds according to the
invention, without the enumeration being restricted to certain species.

[0450] If the compounds according to the invention are applied to the soil
surface before germination, the weed seedlings are either prevented
completely from emerging or else the weeds grow until they have reached
the cotyledon stage, but then their growth stops, and, eventually, after
three to four weeks have elapsed, they die completely.

[0451] If the active compounds are applied post-emergence to the green
parts of the plants, growth stops after the treatment, and the harmful
plants remain at the growth stage of the point of time of application, or
they die completely after a certain time, so that in this manner
competition by the weeds, which is harmful to the crop plants, is
eliminated very early and in a sustained manner.

[0452] Although the compounds according to the invention display an
outstanding herbicidal activity against monocotyledonous and
dicotyledonous weeds, crop plants of economically important crops, for
example dicotyledonous crops of the genera Arachis, Beta, Brassica,
Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea,
Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum,
Vicia, or monocotyledonous crops of the genera Allium, Ananas, Asparagus,
Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale,
Triticum, Zea, in particular Zea and Triticum, are damaged only to an
insignificant extent, or not at all, depending on the structure of the
respective compound according to the invention and its application rate.
This is why the present compounds are highly suitable for the selective
control of unwanted plant growth in plant crops such as agriculturally
useful plants or ornamentals.

[0453] Moreover, the compounds according to the invention (depending on
their respective structure and the application rate applied) have
outstanding growth-regulatory properties in crop plants. They engage in
the plant's metabolism in a regulatory fashion and can therefore be
employed for the influencing, in a targeted manner, of plant constituents
and for facilitating harvesting, such as, for example, by triggering
desiccation and stunted growth. Moreover, they are also suitable for
generally controlling and inhibiting unwanted vegetative growth without
destroying the plants in the process. Inhibiting the vegetative growth
plays an important role in many monocotyledonous and dicotyledonous crops
since for example lodging can be reduced, or prevented completely,
hereby.

[0454] By virtue of their herbicidal and plant-growth-regulatory
properties, the active compounds can also be employed for controlling
harmful plants in crops of genetically modified plants or plants modified
by conventional mutagenesis. In general, the transgenic plants are
distinguished by especially advantageous properties, for example by
resistances to certain pesticides, mainly certain herbicides, resistances
to plant diseases or causative organisms of plant diseases, such as
certain insects or microorganisms such as fungi, bacteria or viruses.
Other specific characteristics relate, for example, to the harvested
material with regard to quantity, quality, storability, composition and
specific constituents. Thus, transgenic plants are known whose starch
content is increased, or whose starch quality is altered, or those where
the harvested material has a different fatty acid composition.

[0455] With regard to transgenic crops, it is preferred to use the
compounds according to the invention in economically important transgenic
crops of useful plants and ornamentals, for example of cereals such as
wheat, barley, rye, oats, millet, rice and corn or else crops of sugar
beet, cotton, soybean, oilseed rape, potato, tomato, peas and other
vegetable varieties.

[0456] It is preferred to employ the compounds according to the invention
as herbicides in crops of useful plants which are resistant, or have been
made resistant by recombinant means, to the phytotoxic effects of the
herbicides.

1. Pre-Emergence Herbicidal Effect and Crop Plant Compatibility

[0457] Seeds of monocotyledonous or dicotyledonous weed plants or crop
plants are placed in sandy loam in wood-fiber pots and covered with soil.
The compounds according to the invention, formulated in the form of
wettable powders (WP), are then applied as aqueous suspension at a water
application rate of 600 I/ha (converted) with the addition of 0.2% of
wetting agent to the surface of the covering soil.

[0458] After the treatment, the pots are placed in a greenhouse and kept
under good growth conditions for the test plants. After about 3 weeks,
the effect of the preparations is scored visually in comparison with
untreated controls (herbicidal effect in percent (%): 100% activity=the
plants have died, 0% activity=like control plants).

[0459] As shown by the results, the compounds according to the invention
have good herbicidal pre-emergence activity against a broad spectrum of
weed grasses and broad-leaved weeds. The compounds Nos. 11, 14, 131, 44,
65, 66, 203, 2517 and other compounds from Tables 1-3, for example, have
very good herbicidal activity against harmful plants such as, for
example, Echinochloa crus galli, Lolium multiflorum, Veronica persica and
Alopecurus myosuroides when applied by the pre-emergence method at an
application rate of 0.32 kg and less of active substance per hectare.

[0460] In addition, compounds according to the invention applied by the
pre-emergence method also spare dicotyledonous crops such as oilseed rape
even at high active compound application rates. Some substances also
spare gramineous crops such as wheat and corn. Some of the compounds
according to the invention have high selectivity and are therefore
suitable for controlling unwanted vegetation in agricultural crops by the
pre-emergence method.

2. Post-Emergence Herbicidal Effect and Crop Plant Compatibility

[0461] Seeds of monocotyledonous and dicotyledonous weed and crop plants
are placed in sandy loam in wood-fiber pots, covered with soil and
cultivated in a greenhouse under good growth conditions. 2 to 3 weeks
after sowing, the test plants are treated at the one-leaf stage. The
compounds according to the invention, formulated in the form of wettable
powders (WP), are then sprayed as aqueous suspension at a water
application rate of 600 I/ha (converted) with the addition of 0.2% of
wetting agent onto the green parts of the plants. After the test plants
have been kept in the greenhouse under optimum growth conditions for
about 3 weeks, the activity of the preparations is rated visually in
comparison to untreated controls (herbicidal activity in percent (%):
100% activity=the plants have died, 0% activity=like control plants).

[0462] As shown by the results, the compounds according to the invention
have good herbicidal post-emergence activity against a plurality of weed
grasses and broad-leaved weeds. The compounds Nos. 44, 65, 131, 203, 2517
and other compounds from Tables 1-3, for example, have very good
herbicidal activity against harmful plants such as, for example,
Echinochloa crus galli and Lolium multiflorum when applied by the
post-emergence method at an application rate of 0.32 kg and less of
active substance per hectare.

[0463] In addition, compounds according to the invention applied by the
post-emergence method also spare dicotyledonous crops such as oilseed
rape even at high active compound application rates. Some substances also
spare gramineous crops such as wheat and corn. Some of the compounds
according to the invention have high selectivity and are therefore
suitable for controlling unwanted vegetation in agricultural crops by the
post-emergence method.